Статті в журналах: "Bioisosteres of benzene"

1

Mykhailiuk, Pavel K. "Saturated bioisosteres of benzene: where to go next?" Organic & Biomolecular Chemistry 17, no. 11 (2019): 2839–49. http://dx.doi.org/10.1039/c8ob02812e.

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2

Wei, Yunlong, Zhiqi Chen, Chen Zhu, Zhen Wu, Yaohui Xu та Xinxin Wu. "Radical Carbosulfonylation of Propellane: Synthesis of Sulfonyl β-Keto-bicyclo[1,1,1]pentanes". Synthesis 53, № 18 (16 квітня 2021): 3325–32. http://dx.doi.org/10.1055/a-1484-1028.

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AbstractThe construction of multiply functionalized bicyclo[1.1.1]pentanes (BCPs) is of high synthetic value, as they are frequently harnessed as bioisosteres of 1,3-disubstituted benzene rings, alkynes, and tert-butyl groups in medicinal chemistry. Herein, we disclose a practical radical-mediated carbosulfonylation of propellane for the synthesis of sulfonyl β-keto-substituted BCPs by using vinyl sulfonates as dual-function reagent. This protocol features broad functional group tolerance and excellent atom-economy, leading to a variety of valuable difunctionalized BCP derivatives under mild photochemical conditions.

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3

Zhao, Jin-Xin, Yu-Xuan Chang, Chi He, Benjamin J. Burke, Michael R. Collins, Matthew Del Bel, Jeff Elleraas, et al. "1,2-Difunctionalized bicyclo[1.1.1]pentanes: Long–sought-after mimetics for ortho/meta-substituted arenes." Proceedings of the National Academy of Sciences 118, no. 28 (July 8, 2021): e2108881118. http://dx.doi.org/10.1073/pnas.2108881118.

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The development of a versatile platform for the synthesis of 1,2-difunctionalized bicyclo[1.1.1]pentanes to potentially mimic ortho/meta-substituted arenes is described. The syntheses of useful building blocks bearing alcohol, amine, and carboxylic acid functional handles have been achieved from a simple common intermediate. Several ortho- and meta-substituted benzene analogs, as well as simple molecular matched pairs, have also been prepared using this platform. The results of in-depth ADME (absorption, distribution, metabolism, and excretion) investigations of these systems are presented, as well as computational studies which validate the ortho- or meta-character of these bioisosteres.

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4

Karmacharya, Ujjwala, Diwakar Guragain, Prakash Chaudhary, Jun-Goo Jee, Jung-Ae Kim, and Byeong-Seon Jeong. "Novel Pyridine Bioisostere of Cabozantinib as a Potent c-Met Kinase Inhibitor: Synthesis and Anti-Tumor Activity against Hepatocellular Carcinoma." International Journal of Molecular Sciences 22, no. 18 (September 7, 2021): 9685. http://dx.doi.org/10.3390/ijms22189685.

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Two novel bioisosteres of cabozantinib, 3 and 4, were designed and synthesized. The benzene ring in the center of the cabozantinib structure was replaced by trimethylpyridine (3) and pyridine (4), respectively. Surprisingly, the two compounds showed extremely contrasting mesenchymal–epithelial transition factor (c-Met) inhibitory activities at 1 μM concentration (4% inhibition of 3 vs. 94% inhibition of 4). The IC50 value of compound 4 was 4.9 nM, similar to that of cabozantinib (5.4 nM). A ligand-based docking study suggested that 4 includes the preferred conformation for the binding to c-Met in the conformational ensemble, but 3 does not. The anti-proliferative activity of compound 4 against hepatocellular carcinoma (Hep3B and Huh7) and non-small-cell lung cancer (A549 and H1299) cell lines was better than that of cabozantinib, whereas 3 did not show a significant anti-proliferative activity. Moreover, the tumor selectivity of compound 4 toward hepatocellular carcinoma cell lines was higher than that of cabozantinib. In the xenograft chick tumor model, compound 4 inhibited Hep3B tumor growth to a much greater extent than cabozantinib. The present study suggests that compound 4 may be a good therapeutic candidate against hepatocellular carcinoma.

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5

Diepers, H. Erik, and Johannes C. L. Walker. "(Bio)isosteres of ortho- and meta-substituted benzenes." Beilstein Journal of Organic Chemistry 20 (April 19, 2024): 859–90. http://dx.doi.org/10.3762/bjoc.20.78.

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Saturated bioisosteres of substituted benzenes offer opportunities to fine-tune the properties of drug candidates in development. Bioisosteres of para-benzenes, such as those based on bicyclo[1.1.1]pentane, are now very common and can be used to increase aqueous solubility and improve metabolic stability, among other benefits. Bioisosteres of ortho- and meta-benzenes were for a long time severely underdeveloped by comparison. This has begun to change in recent years, with a number of potential systems being reported that can act as bioisosteres for these important fragments. In this review, we will discuss these recent developments, summarizing the synthetic approaches to the different bioisosteres as well as the impact they have on the physiochemical and biological properties of pharmaceuticals and agrochemicals.

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6

Denisenko, Aleksandr, Pavel Garbuz, Svetlana V. Shishkina, Nataliya M. Voloshchuk, and Pavel K. Mykhailiuk. "Saturated Bioisosteres of ortho ‐Substituted Benzenes." Angewandte Chemie 132, no. 46 (August 18, 2020): 20696–702. http://dx.doi.org/10.1002/ange.202004183.

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7

Denisenko, Aleksandr, Pavel Garbuz, Svetlana V. Shishkina, Nataliya M. Voloshchuk, and Pavel K. Mykhailiuk. "Saturated Bioisosteres of ortho ‐Substituted Benzenes." Angewandte Chemie International Edition 59, no. 46 (August 18, 2020): 20515–21. http://dx.doi.org/10.1002/anie.202004183.

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8

Chalmers, Benjamin A., Hui Xing, Sevan Houston, Charlotte Clark, Sussan Ghassabian, Andy Kuo, Benjamin Cao, et al. "Validating Eaton's Hypothesis: Cubane as a Benzene Bioisostere." Angewandte Chemie International Edition 55, no. 11 (February 5, 2016): 3580–85. http://dx.doi.org/10.1002/anie.201510675.

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9

Chalmers, Benjamin A., Hui Xing, Sevan Houston, Charlotte Clark, Sussan Ghassabian, Andy Kuo, Benjamin Cao, et al. "Validating Eaton's Hypothesis: Cubane as a Benzene Bioisostere." Angewandte Chemie 128, no. 11 (February 5, 2016): 3644–49. http://dx.doi.org/10.1002/ange.201510675.

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10

Bergamaschi, Enrico, and Christopher Teskey. "Synthese im Blickpunkt: Bioisosteres of meta‐substituted benzenes." Nachrichten aus der Chemie 71, no. 3 (February 28, 2023): 68–71. http://dx.doi.org/10.1002/nadc.20234133609.

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11

Silva, Pedro J. "Will 1,2-dihydro-1,2-azaborine-based drugs resist metabolism by cytochrome P450 compound I?" PeerJ 4 (July 28, 2016): e2299. http://dx.doi.org/10.7717/peerj.2299.

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1,2-dihydro-1,2-azaborine is a structural and electronic analogue of benzene which is able to occupy benzene-binding pockets in T4 lysozyme and has been proposed as suitable arene-mimicking group for biological and pharmaceutical applications. Its applicability in a biological context requires it to be able to resist modification by xenobiotic-degrading enzymes like the P450 cytochromes. Quantum chemical computations described in this work show that 1,2-dihydro-1,2-azaborine is much more prone to modification by these enzymes than benzene, unless steric crowding of the ring prevents it from reaching the active site, or otherwise only allows reaction at the less reactive C4-position. This novel heterocyclic compound is therefore expected to be of limited usefulness as an aryl bioisostere.

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12

Chalmers, Benjamin A., Hui Xing, Sevan Houston, Charlotte Clark, Sussan Ghassabian, Andy Kuo, Benjamin Cao, et al. "Berichtigung: Validating Eaton's Hypothesis: Cubane as a Benzene Bioisostere." Angewandte Chemie 130, no. 28 (July 6, 2018): 8491. http://dx.doi.org/10.1002/ange.201711161.

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13

Chalmers, Benjamin A., Hui Xing, Sevan Houston, Charlotte Clark, Sussan Ghassabian, Andy Kuo, Benjamin Cao, et al. "Corrigendum: Validating Eaton's Hypothesis: Cubane as a Benzene Bioisostere." Angewandte Chemie International Edition 57, no. 28 (July 5, 2018): 8359. http://dx.doi.org/10.1002/anie.201711161.

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14

Jiang, Zhigan, Yan Wang, Wenya Wang, Shengzheng Wang, Bo Xu, Guorong Fan, Guoqiang Dong, et al. "Discovery of highly potent triazole antifungal derivatives by heterocycle-benzene bioisosteric replacement." European Journal of Medicinal Chemistry 64 (June 2013): 16–22. http://dx.doi.org/10.1016/j.ejmech.2013.04.025.

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15

Melnykov, Kostiantyn, Oleksii Pidvyshennyi, Oleh Smyrnov, and Oleksandr O. Grygorenko. "Aromatic sulfoximines with fluorinated alkyl side chains: scalable synthesis and effects of structural elements on lipophilicity." Bulletin of Taras Shevchenko National University of Kyiv. Chemistry, no. 1 (59) (2024): 5–9. https://doi.org/10.17721/1728-2209.2024.1(59).1.

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Background. Sulfoximines recently gained significant attention of researchers as bioisosteric analogs of sulfone, amide, sulfonamide, and other related structural fragments. On the other hand, incorporation of fluorine atoms is a well-known tool in medicinal chemistry allowing to improve pharmacokinetic and physicochemical parameters of biologically active compounds. Therefore, development of effective approaches towards fluorine-containing sulfoximines, in particular, with additional functional groups, as well as establishing effects of their structure on the main physicochemical properties, is an important task. The goal of this work is to develop scalable protocols for the synthesis of 1-bromo-4-(S-(fluoroalkyl)sulfonimidoyl)benzenes and to establish effect of the fluorine atoms and the sulfoximine fragment on lipophilicity (as compared to the non-fluorinated analogs and the corresponding sulfones). Objects. Aromatic sulfoximines and sulfones with fluorinated alkyl side chains. Methods. Scalable organic synthesis of aromatic sulfoximines with fluorinated alkyl side chains; structure investigation and characterization of the synthesized compounds by 1H, 19F, 13C NMR spectroscopy and chromatomass-spectrometry; lipophilicity measurement by liquid-liquid extraction in combination with HPLC. Results. Based on the known approach to the sulfoximine synthesis that includes introduction of the imine fragment by oxidation of the corresponding aryl fluoroalkyl sulfide with phenyliodosodiacetate in the presence of ammonium carbamate, scalable protocols for the synthesis of 1-bromo-4-(S-(fluoroalkyl)sulfonimidoyl)benzenes were developed (fluoroalkyl – CH2F, CHF2, CF3). Using liquid-liquid extraction in combination with HPLC (“shake-flask” protocol), lipophilicity of the obtained compounds (i.e., 1-octanol – water distribution coefficient logarithm, LogP) was determined and compared with the values for the non-fluorinated analogs and the corresponding sulfones. Conclusions. It is shown that the approach to the synthesis of sulfoximines that includes oxidation of the corresponding alkyl aryl sulfide with phenyliodosodiacetate in the presence of ammonium carbamate, is efficient to obtain fluorinated derivatives in multigram quantities. It is found that fluorination of 1-bromo-4-(S-methylsulfonimidoyl)benzene at the methyl group leads to the stepwise increase the molecule’s lipophilicity (by ca. 0.6 LogP units per each fluorine atom on average), while replacement of the sulfone moiety with sulfoximine in the studied series lowers it by ca. 0.7 LogP units.

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16

Kmoníček, Vojtěch, Emil Svátek, Jiří Holubek, Miroslav Ryska, Martin Valchář, and Miroslav Protiva. "Synthesis of 1-acyl- and 1-(thioacyl)-4-benzylpiperazines as potential antidepressants." Collection of Czechoslovak Chemical Communications 55, no. 7 (1990): 1817–27. http://dx.doi.org/10.1135/cccc19901817.

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2-Nitro, 3-nitro- and 4-nitrobenzoyl chloride were reacted with 1-benzylpiperazine in benzene in the presence of triethylamine and gave the amides IV-VI, the first of which is considered a bioisostere of the antidepressant agent piberaline (I). 2-Dimethylamino-, 3-dimethylamino- and 4-dimethylaminobenzoic acid were treated with thionyl chloride in benzene in the presence of triethylamine or pyridine, and the acid chlorides formed were reacted in situ with 1-benzylpiperazine affording the amides VII-IX. The amides I and IV-VI were transformed by treatment with phosphorus pentasulfide in pyridine to the thioamides X-XIII. 4-(Dimethylaminomethyl)benzoic acid was reacted with 1-benzylpiperazine in dimethylformamide in the presence of N,N'-carbonyldiimidazole and afforded the amide XIV. Heating of ethyl 5-methylimidazole-4-carboxylate with 1-benzylpiperazine to 200-210 °C gave the amide XV together with the unexpected 1-benzyl-4-ethylpiperazine (XVI). The oily or crystalline bases of the amino amides or thioamides were mostly transformed to crystalline salts and characterized by spectra. Out of the compounds prepared only X (V⁄FB-17 070) and XIV (V⁄FB-17 114) showed indications of efficacy in tests which are considered indicative of antidepressant activity. Compounds VII, VIII, and X appeared to be mildly antidopaminergic - similarly like piberaline (I), and compounds IV, V, XI, XIV, and XV on the contrary showed signs of dopaminominetic activity.

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17

Makarov, Ilya S., Cara E. Brocklehurst, Konstantin Karaghiosoff, Guido Koch, and Paul Knochel. "Synthesis of Bicyclo[1.1.1]pentane Bioisosteres of Internal Alkynes and para ‐Disubstituted Benzenes from [1.1.1]Propellane." Angewandte Chemie International Edition 56, no. 41 (August 30, 2017): 12774–77. http://dx.doi.org/10.1002/anie.201706799.

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18

Šoškić, V., and Jelena Joksimović. "Bioisosteric Approach In The Design of New Dopaminergic/ Serotonergic Ligands." Current Medicinal Chemistry 5, no. 6 (December 1998): 493–512. http://dx.doi.org/10.2174/0929867305666220319113953.

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Dopaminergic and serotonergic ligands are widely applied in the therapy of some severe diseases in humans connected to the malfunctioning of the corresponding membrane receptors within the CNS. However, no pharmaceuticals of this type with an ideal therapeutic index have been synthesized so far and there is a constant need of producing new dopaminergic/serotonergic ligands with improved properties especially with regard to undesirable side effects expressed after a prolonged therapy. Dopaminergic/serotonergic ratio turned out to be important for a fine tuning of pharmacological profile of new ligands. Employing a bioisosteric approach, we have synthesized numerous quinoxalinediones, benztriazoles, benzimidazoles and 2-substituted benzimidazoles as potential dopaminergic and/or . mixed dopaminergic/serotonergic compounds. With this purpose, benzimidazole and its derivatives were incorporated into phenylethylamine, 3- and 4-substituted phenylethylpiperidine, 1- substituted 4-arylpiperazine and semirigid 2-aminotetralin frame and the resulting ligands were checked for the binding affinity at the D1 and D2 dopamine and 5-HT1 A serotonin receptors in radioligand binding assays in vitro. Synaptosomal membranes prepared from bovine caudate nuclei and hippocampi served as a source of the dopamine and serotonin receptors, respectively. [3H]SCH 23390 (D1 receptor-selective}, [3H]spiperone (D2 receptor-selective) and 8-0H-[3H]DPAT (5-HT1 A receptor-selective) were employed as radioligands in competition binding assays. Properties of substituents introduced into position 2 of benzimidazole ring, as well as the nature of the frame into which benzimidazole pharmacophorwas incorporated have been shown to determine ligand binding affinity, mode of action and receptor preference, i.e. dopaminergic/serotonergic affinity ratio. Benzimidazolyl-2-thione and benztriazole derivatives were the most potent dopaminergic/serotonergic ligands. Molecular ab initio calculations of the electronic properties of pharmacophoric entities of the new ligands revealed different electron density distribution around the benzene ring in the active and inactive ligands. It can be assumed that this difference influences the properties of 7t- 7t interactions in a receptor-ligand complex. The results are discussed in comparison with the data of other authors working on similar topics.

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19

Serban. "Future Prospects in the Treatment of Parasitic Diseases: 2-Amino-1,3,4-Thiadiazoles in Leishmaniasis." Molecules 24, no. 8 (April 19, 2019): 1557. http://dx.doi.org/10.3390/molecules24081557.

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Neglected tropical diseases affect the lives of a billion people worldwide. Among them, the parasitic infections caused by protozoan parasites of the Trypanosomatidae family have a huge impact on human health. Leishmaniasis, caused by Leishmania spp., is an endemic parasitic disease in over 88 countries and is closely associated with poverty. Although significant advances have been made in the treatment of leishmaniasis over the last decade, currently available chemotherapy is far from satisfactory. The lack of an approved vaccine, effective medication and significant drug resistance worldwide had led to considerable interest in discovering new, inexpensive, efficient and safe antileishmanial agents. 1,3,4-Thiadiazole rings are found in biologically active natural products and medicinally important synthetic compounds. The thiadiazole ring exhibits several specific properties: it is a bioisostere of pyrimidine or benzene rings with prevalence in biologically active compounds; the sulfur atom increases lipophilicity and combined with the mesoionic character of thiadiazoles imparts good oral absorption and good cell permeability, resulting in good bioavailability. This review presents synthetic 2-amino-1,3,4-thiadiazole derivatives with antileishmanial activity. Many reported derivatives can be considered as lead compounds for the synthesis of future agents as an alternative to the treatment of leishmaniasis.

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20

Bär, Robin M., Gregor Heinrich, Martin Nieger, Olaf Fuhr, and Stefan Bräse. "Insertion of [1.1.1]propellane into aromatic disulfides." Beilstein Journal of Organic Chemistry 15 (May 28, 2019): 1172–80. http://dx.doi.org/10.3762/bjoc.15.114.

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Herein we present the synthesis of symmetrically and unsymmetrically substituted 1,3-bissulfanylbicyclo[1.1.1]pentanes from disulfides and [1.1.1]propellane. Bicyclo[1.1.1]pentanes (BCPs) recently gained interest as rigid linkers and as bioisosters of para-substituted benzene and alkyne moieties. The most promising precursor for BCPs is [1.1.1]propellane (1). The available methods to synthesize BCPs are quite limited and many groups contribute to the development of novel methods. The insertion of 1 into disulfide bonds is known, but has never been thoroughly investigated. In this study, we show that an UV initiated radical reaction can be used to synthesize symmetrically and unsymmetrically substituted BCP sulfides by reaction of [1.1.1]propellane (1) with disulfides. Depending on the ratio of 1 to the disulfide, only the BCP product (with up to 98% yield) or a mixture of BCP and [2]staffane can be obtained. The reaction tolerates functional groups such as halogens, alkyl and methoxy groups. The separation of the corresponding BCP and [2]staffane products is challenging but possible by column chromatography and preparative TLC in most cases. Single crystal X-ray diffraction analysis confirms the rod-like structure of the [2]staffanes that is often required in material applications.

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21

Foldesi, Tamas, Balazs Volk, and Matyas Milen. "A Review of 2,3-Benzodiazepine-related Compounds: Diazepines and 1,2,5- Triazepines Fused with Five-membered Nitrogen Heterocycles." Current Organic Synthesis 15, no. 6 (August 29, 2018): 729–54. http://dx.doi.org/10.2174/1570179415666180601101856.

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Background: 2,3-Benzodiazepines represent an important class of biologically active compounds, some members of this family have reached the human clinical stage. With formal bioisosteric replacement of the benzene ring to five-membered nitrogen heterocycles, several new diazepine and 1,2,5-triazepine derivatives have been synthesized in the past 30 years. Objective: Investigations in the field of heterocyclic chemistry is very important, because there could be several new medicines among the newly synthesized heterocyclic ring systems, which could be used against several diseases which have no remedy yet, for example some types of cancer. The research on antibacterial compounds is also an important field because of spreading of multiresistant pathogens. This review aims to summarize the literature of certain 2,3-benzodiazepine analogues. Conclusion: After a brief historical introduction, various ring systems containing a 2,3-diazepine or a 1,2,5- triazepine ring condensed with five-membered nitrogen heterocycles are disclosed. First, pyrrole-fused compounds are introduced, followed by indole and carbazole derivatives. After that, diverse ring systems containing an imidazole ring are presented. The review is closed with the chemistry of some interesting triazole and tetrazole derivatives. Many of these compounds bear significant biological efficacy.

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22

Karaaslan, Cigdem, Yalcin Duydu, Aylin Ustundag, Can O. Yalcin, Banu Kaskatepe, and Hakan Goker. "Synthesis & Anticancer Evaluation of New Substituted 2-(3,4- Dimethoxyphenyl)benzazoles." Medicinal Chemistry 15, no. 3 (April 12, 2019): 287–97. http://dx.doi.org/10.2174/1573406414666180711130012.

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Background: The benzazole nucleus is found in many promising small molecules such as anticancer and antibacterial agents. Bendamustine (Alkylating agent), Nocodazole (Mitotic inhibitor), Veliparib (PARP inhibitor), and Glasdegib (SMO inhibitor) are being clinically used as anticancer therapeutic which bear benzimidazole moiety. Based on the principle of bioisosterism, in the present work, 23 compounds belonging to 2-(3,4-dimethoxyphenyl)benzazoles and imidazopyridine series were synthesized and evaluated for their anticancer and antimicrobial activities. Objective: A series of new 2-(3,4-dimethoxyphenyl)-1H-benz(or pyrido)azoles were synthesized and evaluated for their anticancer and antimicrobial activities. Method: N-(5-chloro-2-hdroxyphenyl)-3,4-dimethoxybenzamide 1, was obtained by the amidation of 2-hydroxy-5-chloroaniline with 3,4-dimethoxybenzoic acid by using 1,1&'-carbonyldiimidazole. Cyclization of 1 to benzoxazole derivative 2, was achieved by p-toluenesulfonic acid. Other 1H-benz(or pyrido)azoles were prepared by the reaction between 2-aminothiophenol, ophenylenediamine, o-pyridinediamine with sodium metabisulfite adduct of 3,4-dimethoxybenzaldehyde. The NMR assignments of the dimethoxy groups were established by the NOESY spectra. Results: Compound 12, bearing two chlorine atoms at the 5(4) and 7(6) positions of the benzene moiety of benzimidazole was found the most potent analogue against A549 cells with the GI50 value of 1.5 μg/mL. Moreover, 24 showed remarkable cell growth inhibition against MCF-7 and HeLa cells with the GI50 values of 7 and 5.5 μg/mL, respectively. The synthesized compounds have no important antibacterial and antifungal activities. Conclusion: It could be concluded that the introduction of di-chloro atoms at the phenyl ring of 2-(3,4-dimethoxyphenyl)-1H-benzimidazoles increases significant cytotoxicity to selected human tumor cell lines in comparison to other all benzazoles synthesized. Unsubstituted 2-(3,4- dimethoxyphenyl)-imidazopyridines also gave good inhibitory profile against A549 and HeLa cells.

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23

Hsu, Chih-Wei, Chun-Fu Wu, Yung-Chi Lee, and Woo-Jin Yoo. "Synthesis of 2‐Substituted Bicyclo[2.1.1]hexan‐1‐ols via SmI2‐Mediated Reductive Cyclization Reactions." Advanced Synthesis & Catalysis, August 16, 2024. http://dx.doi.org/10.1002/adsc.202400891.

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The replacement of benzene rings with saturated bioisosteric counterparts is a key priority in drug discovery programs, and disubstituted bicyclo[2.1.1]hexanes have been recognized as flexible molecular scaffolds that could act as ortho‐substituted benzene bioisosteres. In this study, we outline the synthesis of a wide range of 2‐substituted bicyclo[2.1.1]hexan‐1‐ols, which have the potential to emulate ortho‐phenolic derivatives, via SmI2‐mediated reductive cyclization reactions. The synthetic utility of this methodology was exemplified by the preparation of several saturated analogs of pharmaceutically relevant compounds.

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24

Nagasawa, Shota, and Yoshiharu Iwabuchi. "Recent Progress in Accessing Multi-functionalized Caged Hydrocarbons: En Route to Highly-Functionalized Saturated (Bio)isosteres of Benzene Ring." Synthesis, July 4, 2024. http://dx.doi.org/10.1055/a-2360-8218.

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Recently, many saturated bioisosteres of benzene ring have been developed, and their application in drug development has been evaluated. Most of these are caged hydrocarbons, which have rigid skeletons and three-dimensional spaces. Recent efforts to synthesize these caged hydrocarbons have enabled access to multi-functionalized congeners that are expected to be (bio)isosteres of multi-functionalized benzenes. This review article summarizes recently reported methods to obtain multi-functionalized (typically more than disubstituted) caged hydrocarbons.

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25

Wiesenfeldt, Mario P., James A. Rossi-Ashton, Ian B. Perry, Johannes Diesel, Olivia L. Garry, Florian Bartels, Susannah C. Coote, et al. "General Access to Cubanes as Benzene Bioisosteres." Nature, April 4, 2023. http://dx.doi.org/10.1038/s41586-023-06021-8.

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26

Nugent, Jeremy, Adrián López-Francés, Alistair J. Sterling, Min Yi Tay, Nils Frank, James Mousseau, Fernanda Duarte та Edward A. Anderson. "α-Amino Bicycloalkylation through Organophotoredox Catalysis". Chemical Science, 2024. http://dx.doi.org/10.1039/d4sc01368a.

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Bridged bicycloalkanes such as bicyclo[1.1.1]pentanes (BCPs) and bicyclo[3.1.1]heptanes (BCHeps) are important motifs in contemporary drug design due to their potential to act as bioisosteres of disubstituted benzene rings, often resulting...

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27

Denisenko, Aleksandr, Pavel Garbuz, Yelyzaveta Makovetska, Oleh Shablykin, Dmytro Lesyk, Galeb Al-Maali, Rodion Korzh, Iryna V. Sadkova, and Pavel K. Mykhailiuk. "1,2-Disubstituted Bicyclo[2.1.1]hexanes as Saturated Bioisosteres of the ortho-substituted Benzene." Chemical Science, 2023. http://dx.doi.org/10.1039/d3sc05121h.

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Bicyclo[2.1.1]hexanes have been synthesized, characterized, and biologically validated as saturated bioisosteres of the ortho-substituted benzene ring. The incorporation of the 1,2 disubstituted bicyclo[2.1.1]hexane core into the structure of fungicides Boscalid...

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28

Takebe, Hiyori, and Seijiro Matsubara. "Cuneanes –The Potential as Benzene Bioisosteres Having Chirality." Synthesis, August 26, 2024. http://dx.doi.org/10.1055/a-2403-1860.

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Cuneane, a structural isomer of cubane, possesses C2v symmetry, unlike the Oh symmetry of cubane. It can exhibit chirality with even a single substituent, differentiating it from cubane. Consequently, cuneane is being explored as a potential benzene bioisostere in pharmaceutical molecules, adding complexity such as chirality through the isomerization of the cubane skeleton. Although there has been limited research on the synthesis of cuneane in the past, recent years have seen increased attention to this cage hydrocarbon. This discussion will cover the synthesis, utilization, and further transformation reactions of the cuneane framework into other cage hydrocarbons in recent years.

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29

Tsien, Jet, Chao Hu, Rohan R. Merchant, and Tian Qin. "Three-dimensional saturated C(sp3)-rich bioisosteres for benzene." Nature Reviews Chemistry, July 9, 2024. http://dx.doi.org/10.1038/s41570-024-00623-0.

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30

Hu, Qian-Qian, Liu-Yang Wang, Xing-Hao Chen, Ze-Xiang Geng, Jie Chen, and Ling Zhou. "Lewis Acid Catalyzed Cycloaddition of Bicyclobutanes with Ynamides for the Synthesis of Polysubstituted 2‐Amino‐bicyclo[2.1.1]hexenes." Angewandte Chemie, May 23, 2024. http://dx.doi.org/10.1002/ange.202405781.

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Synthesis of bicyclic scaffolds has gained significant attention in drug discovery due to their potential to mimic benzene bioisosteres. Here, we present a mild and scalable Sc(OTf)3‐catalyzed [3+2] cycloaddition of bicyclo[1.1.0]butanes (BCBs) with ynamides, yielding a diverse array of polysubstituted 2‐amino‐bicyclo[2.1.1]hexenes in good to excellent yields. These products offer valuable starting materials for the construction of novel functionalized bicyclo[1.1.0]butanes. Preliminary mechanistic studies indicate that the reaction involves a nucleophilic addition of ynamides to bicyclo[1.1.0]butanes, followed by an intramolecular cyclization of in situ generated enolate and keteniminium ion. We expect that these findings will encourage utilization of complex bioisosteres and foster further investigation into BCB‐based cycloaddition chemistry.

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31

Hu, Qian-Qian, Liu-Yang Wang, Xing-Hao Chen, Ze-Xiang Geng, Jie Chen, and Ling Zhou. "Lewis Acid Catalyzed Cycloaddition of Bicyclobutanes with Ynamides for the Synthesis of Polysubstituted 2‐Amino‐bicyclo[2.1.1]hexenes." Angewandte Chemie International Edition, May 23, 2024. http://dx.doi.org/10.1002/anie.202405781.

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Анотація:

Synthesis of bicyclic scaffolds has gained significant attention in drug discovery due to their potential to mimic benzene bioisosteres. Here, we present a mild and scalable Sc(OTf)3‐catalyzed [3+2] cycloaddition of bicyclo[1.1.0]butanes (BCBs) with ynamides, yielding a diverse array of polysubstituted 2‐amino‐bicyclo[2.1.1]hexenes in good to excellent yields. These products offer valuable starting materials for the construction of novel functionalized bicyclo[1.1.0]butanes. Preliminary mechanistic studies indicate that the reaction involves a nucleophilic addition of ynamides to bicyclo[1.1.0]butanes, followed by an intramolecular cyclization of in situ generated enolate and keteniminium ion. We expect that these findings will encourage utilization of complex bioisosteres and foster further investigation into BCB‐based cycloaddition chemistry.

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32

Wang, Yuying, Jianyang Dong, and Dong Xue. "Metal- and Photocatalyst-Free Sulfonylcyanation of [1.1.1]Propellane with Sulfonyl Cyanide." Current Organic Synthesis 22 (November 14, 2024). http://dx.doi.org/10.2174/0115701794347153241107110324.

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Background: Bicyclo[1.1.1]pentanes (BCPs), recognized as bioisosteres for para-disubstituted benzene rings, have gained prominence as valuable bioactive scaffolds in drug research. Methods: This study describes a radical-coupling method for the synthesis of sulfonyl-, cy-ano-substituted BCPs from sulfonyl cyanide and [1.1.1]propellane. In this study, the synthet-ic schemes were designed to show the chemical reactions. Nuclear Magnetic Resonance (NMR) and Mass Spectrometry (MS) were used to identify and characterize the final com-pounds. Results: This method does not require photocatalysts, metals, or light, generating BCP ni-triles as a useful building block. The synthetic potential of this mild protocol was showcased by the diverse transformations. Conclusion: This versatile method significantly expands the range of BCP-type bioisosteres that can be generated.

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33

Lindl, Felix, Torsten Thiess, James T. Goettel, Simon Dotzauer, Moritz Johannes Ernst, Guillaume Bélanger‐Chabot, and Holger Braunschweig. "Borole Ring Expansion Reactions with Boron Azides: A Versatile Pathway to Borylated Azaborinines." European Journal of Inorganic Chemistry, November 13, 2024. http://dx.doi.org/10.1002/ejic.202400498.

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AbstractThe reaction of boroles with organic azides is known to straightforwardly yield 1,2‐azaborinines, which have generated significant interest as benzene bioisosteres. We show that this powerful synthetic pattern extends to a variety of structurally and chemically diverse boron azides, including recently reported diborane(4) azides. This provides a general, powerful borylation method to expand the chemistry of 1,2‐azaborinines.

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34

Yasukawa, Tomohiro, Katja S. Håheim, and Janine Cossy. "Functionalization of Cubane Formation of C−C and C−Heteroatom Bonds." Helvetica Chimica Acta, February 2, 2024. http://dx.doi.org/10.1002/hlca.202300200.

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AbstractFunctionalized cubanes are attractive scaffolds for medicinal chemists as they are bioisosteres of benzene rings. The replacement of a benzene ring by a cubane, in a bioactive compound, can have a beneficial effect on the biological activity of such compound. Thus, the design of new molecular cubyl building blocks is of importance. In this review, we will focus on the functionalization of cubanes by creating C−C, C−heteroatom bonds e. g. C−N, C−O, C−B, C−P and C−S bonds. Different methods are reported involving organometallics, radicals, and ionic species. Mechanisms are included when relevant.

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35

Wang, Dongdong, Xiaohong Lyu, Mengtao Sun, and Yongqiang Liang. "Spectral Analysis on Cuba-Lumacaftor: Cubane as Benzene Bioisosteres of Lumacaftor." ACS Omega, November 3, 2023. http://dx.doi.org/10.1021/acsomega.3c07532.

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36

Takebe, Hiyori, Tomomi Umemura, and Seijiro Matsubara. "Constitutional Isomerization of Cubane to Semibullvalene via Cuneane in Hot Water." Chemistry Letters, December 1, 2023. http://dx.doi.org/10.1093/chemle/upad010.

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Abstract The construction of cage-type hydrocarbon scaffolds, potential bioisosteres for benzene, often involves multiple steps, making their selective syntheses challenging. However, by employing a scaffold editing technique that leverages the isomerization of the highly symmetrical cubane as a precursor, these can be synthesized more efficiently with fewer steps. In this study, we present a method for the selective synthesis of semibullvalene-1,3- dicarboxylic acid with a good yield, starting from dimethyl cubane-1,4-dicarboxylate, using a reaction in hot water.

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37

Pattison, Graham. "Assessing the rigidity of cubanes and bicyclo(1.1.1)pentanes as benzene bioisosteres." Bioorganic & Medicinal Chemistry, February 2024, 117652. http://dx.doi.org/10.1016/j.bmc.2024.117652.

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38

Sujansky, Stephen J., and Xiaoshen Ma. "Reaction Paradigms that Leverage Cycloaddition and Ring Strain to Construction Bicyclic Aryl Bioisosteres from Bicyclo[1.1.0]butanes." Asian Journal of Organic Chemistry, February 21, 2024. http://dx.doi.org/10.1002/ajoc.202400045.

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Within a medicinal chemist’s toolbox, one of the most effective strategies to improve the overall properties of a biologically active compound is bioisosteric replacement. Ever since the first example of replacing benzene with a bicyclo[1.1.1]pentane (BCP) group was published in the late 1990s, the medicinal chemistry community has continually been expanding the scope of such phenyl bioisosteric replacements. Recent interest from academia has focused on novel synthetic strategies to access C(sp3)‐rich bicyclic hydrocarbons with expanded ring sizes. Herein, we summarize some of these transformations and reveal that most rely on strain releasing cycloadditions with bicyclo[1.1.0]butane (BCB) and bicyclo[2.1.0]pentane (housane). We have organized this review based on the mechanism of such strain release strategies, namely, carbene cycloadditions, energy transfer photocatalyzed cycloadditions, electron transfer catalyzed cycloadditions, and polar cycloadditions.

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39

He, Heng-Xian, Feng Wu, Xu Zhang, and Jian-Jun Feng. "Ring Expansion toward Fused Diazabicyclo[3.1.1]heptanes through Lewis Acid Catalyzed Highly Selective C−C/C−N Bond Cross‐Exchange Reaction between Bicyclobutanes and Diaziridines." Angewandte Chemie, November 12, 2024. http://dx.doi.org/10.1002/ange.202416741.

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Анотація:

The synthesis of bicyclic scaffolds has garnered considerable interest in drug discovery because of their ability to mimic benzene bioisosteres. Herein, we introduce a new approach that utilizes a Lewis acid (Sc(OTf)3)‐catalyzed σ‐bond cross‐exchange reaction between the C−C bond of bicyclobutanes and the C−N bond of diaziridines to produce multifunctionalized and medicinally interesting azabicyclo[3.1.1]heptane derivatives. The reaction proceeds well with different bicyclobutanes and a broad range of aryl‐ as well as alkenyl‐, but also alkyl‐substituted diaziridines (up to 98% yield). Conducting a scale‐up experiment and exploring the synthetic transformations of the cycloadducts emphasized the practical application of the synthesis. Furthermore, a zinc‐based chiral Lewis acid catalytic system was developed for the enantioselective version of this reaction (up to 96% ee).

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40

He, Heng-Xian, Feng Wu, Xu Zhang, and Jian-Jun Feng. "Ring Expansion toward Fused Diazabicyclo[3.1.1]heptanes through Lewis Acid Catalyzed Highly Selective C−C/C−N Bond Cross‐Exchange Reaction between Bicyclobutanes and Diaziridines." Angewandte Chemie International Edition, November 12, 2024. http://dx.doi.org/10.1002/anie.202416741.

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Анотація:

The synthesis of bicyclic scaffolds has garnered considerable interest in drug discovery because of their ability to mimic benzene bioisosteres. Herein, we introduce a new approach that utilizes a Lewis acid (Sc(OTf)3)‐catalyzed σ‐bond cross‐exchange reaction between the C−C bond of bicyclobutanes and the C−N bond of diaziridines to produce multifunctionalized and medicinally interesting azabicyclo[3.1.1]heptane derivatives. The reaction proceeds well with different bicyclobutanes and a broad range of aryl‐ as well as alkenyl‐, but also alkyl‐substituted diaziridines (up to 98% yield). Conducting a scale‐up experiment and exploring the synthetic transformations of the cycloadducts emphasized the practical application of the synthesis. Furthermore, a zinc‐based chiral Lewis acid catalytic system was developed for the enantioselective version of this reaction (up to 96% ee).

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41

"Transition-Metal-Free Synthesis of Bicyclo[2.1.1]hexan-2-ones – meta- and ortho-Benzene Bioisosteres." Synfacts 19, no. 09 (August 16, 2023): 0926. http://dx.doi.org/10.1055/s-0042-1751999.

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42

Alvarez, Eva Maria, Zibo Bai, Saikat Pandit, Nils Frank, Luca Torkowski, and Tobias Ritter. "O-, N- and C-bicyclopentylation using thianthrenium reagents." Nature Synthesis, March 30, 2023. http://dx.doi.org/10.1038/s44160-023-00277-8.

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AbstractRigid 1,3-disubstituted bicyclo[1.1.1]pentanes (BCPs) are linear bioisosteres for para-substituted benzene rings in drug development and can lead to an improved pharmacokinetic profile. The construction of BCPs commonly requires the cumbersome use of labile [1.1.1]propellane in solution, and more stable reagents do not show the versatile reactivity of propellane itself. Here we report stable thianthrenium-based BCP reagents for practical O-, N- and C-alkylation reactions that expand the scope of bicyclopentylation beyond that of any other reagent, including [1.1.1]propellane. The redox and stereoelectronic properties of the thianthrene scaffold are relevant for both the synthesis of the BCP-thianthrenium reagents via strain release as well as their subsequent reactivity. The weak exocyclic C–S bond can undergo selective mesolytic cleavage upon single-electron reduction to produce BCP radicals that engage in transition metal-mediated C–O, C–N and C–C bond formations, even at a late stage of multistep reactions with a wide variety of functional groups present.

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43

Wang, Ji-Jie, Lei Tang, Yuanjiu Xiao, Wen-Biao Wu, Guoqiang Wang та Jian-Jun Feng. "Switching between the [2π+2σ] and Hetero‐[4π+2σ] Cycloaddition Reactivity of Bicyclobutanes with Lewis Acid Catalysts Enables the Synthesis of Spirocycles and Bridged Heterocycles". Angewandte Chemie, 10 травня 2024. http://dx.doi.org/10.1002/ange.202405222.

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Анотація:

The exploration of the complex chemical diversity of bicyclo[n.1.1]alkanes and their use as benzene bioisosteres has garnered significant attention over the past two decades. Regiodivergent syntheses of thiabicyclo[4.1.1]octanes (S‐BCOs) and highly substituted bicyclo[2.1.1]hexanes (BCHs) using a Lewis acid‐catalyzed formal cycloaddition of bicyclobutanes (BCBs) and 3‐benzylideneindoline‐2‐thione derivatives have been established. The first hetero‐(4+3) cycloaddition of BCBs, catalyzed by Zn(OTf)2, was achieved with a broad substrate scope under mild conditions. In contrast, the less electrophilic BCB ester undergoes a Sc(OTf)3‐catalyzed [2π+2σ] reaction with 1,1,2‐trisubstituted alkenes, yielding BCHs with a spirocyclic quaternary carbon center. Control experiments and preliminary theoretical calculations suggest that the diastereoselective [2π+2σ] product formation may involve a concerted cycloaddition between a zwitterionic intermediate and E‐1,1,2‐trisubstituted alkenes. Additionally, the hetero‐(4+3) cycloaddition may involve a concerted nucleophilic ring‐opening mechanism.

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44

Wang, Ji-Jie, Lei Tang, Yuanjiu Xiao, Wen-Biao Wu, Guoqiang Wang та Jian-Jun Feng. "Switching between the [2π+2σ] and Hetero‐[4π+2σ] Cycloaddition Reactivity of Bicyclobutanes with Lewis Acid Catalysts Enables the Synthesis of Spirocycles and Bridged Heterocycles". Angewandte Chemie International Edition, 10 травня 2024. http://dx.doi.org/10.1002/anie.202405222.

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Анотація:

The exploration of the complex chemical diversity of bicyclo[n.1.1]alkanes and their use as benzene bioisosteres has garnered significant attention over the past two decades. Regiodivergent syntheses of thiabicyclo[4.1.1]octanes (S‐BCOs) and highly substituted bicyclo[2.1.1]hexanes (BCHs) using a Lewis acid‐catalyzed formal cycloaddition of bicyclobutanes (BCBs) and 3‐benzylideneindoline‐2‐thione derivatives have been established. The first hetero‐(4+3) cycloaddition of BCBs, catalyzed by Zn(OTf)2, was achieved with a broad substrate scope under mild conditions. In contrast, the less electrophilic BCB ester undergoes a Sc(OTf)3‐catalyzed [2π+2σ] reaction with 1,1,2‐trisubstituted alkenes, yielding BCHs with a spirocyclic quaternary carbon center. Control experiments and preliminary theoretical calculations suggest that the diastereoselective [2π+2σ] product formation may involve a concerted cycloaddition between a zwitterionic intermediate and E‐1,1,2‐trisubstituted alkenes. Additionally, the hetero‐(4+3) cycloaddition may involve a concerted nucleophilic ring‐opening mechanism.

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45

Smyrnov, Oleh K., Kostiantyn P. Melnykov, Eduard B. Rusanov, Sergey Yu Suikov, Olexandr E., Andrey A. Fokin, Dmytro M. Volochnyuk, and Serhiy V. Ryabukhin. "Multigram Synthesis of Dimethyl Stellane‐1,5‐Dicarboxylate as a Key Precursor for the ortho‐Benzene Mimics." Chemistry – A European Journal, September 20, 2023. http://dx.doi.org/10.1002/chem.202302454.

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Herein we present previously unavailable C(sp3)‐rich polycyclic hydrocarbon scaffolds which have a potential to become valuable tools in medicinal chemistry and crop science as saturated bioisosteres of benzenoids. We have developed a scalable protocol (up to 50 g from a single synthetic run) for the synthesis of tricyclo[3.3.0.03,7]octane (bisnoradamantane or stellane) 1,5‐dicarboxylic acid derivatives. X‐ray crystallographic analysis of the stellane 1,5‐dicarboxylic acid dimethyl ester has revealed that this scaffold is an optimal saturated isostere for ortho‐disubstituted benzene where substituents exhibit the in‐plane topology. The synthetic protocol is based on the oxidative cyclization of dimethyl octahydropentalene‐2,5‐dicarboxylate (DMOD) through lithiation followed by I2 oxidation. The reaction outcome is determined by the stereochemistry of the substrate. While the endo,endo cis‐DMOD, exclusively gives the "unwanted" Claisen cyclization product the exo,endo cis‐ and exo,exo cis‐ stereoisomers afford the desired stellane 1,5‐dicarboxylic acid dimethyl ester quantitatively. DFT computations have revealed that the reaction proceeds via the dianion of dimethyl octahydropentalene‐2,5‐dicarboxylate, which undergoes SET oxidation by I2 to form a radical anion. The subsequent cyclization followed by a second SET oxidation gives desired stellane derivative.

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46

Ma, Xiaoshen, Adam M. Beard, Samantha A. Burgess, Miroslawa Darlak, Justin A. Newman, Lisa M. Nogle, Mark J. Pietrafitta, David A. Smith, Xiao Wang, and Lei Yue. "General Synthesis of Conformationally Constrained Noncanonical Amino Acids with C(sp³)-Rich Benzene Bioisosteres." Journal of Organic Chemistry, March 26, 2024. http://dx.doi.org/10.1021/acs.joc.4c00225.

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47

Prysiazhniuk, Kateryna, Oleksandr P. Datsenko, Oleksandr Polishchuk, Stanislav Shulha, Oleh Shablykin, Yelyzaveta Nikandrova, Kateryna Horbatok, et al. "Spiro[3.3]heptane as a Saturated Benzene Bioisostere**." Angewandte Chemie International Edition, January 22, 2024. http://dx.doi.org/10.1002/anie.202316557.

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AbstractThe spiro[3.3]heptane core, with the non‐coplanar exit vectors, was shown to be a saturated benzene bioisostere. This scaffold was incorporated into the anticancer drug sonidegib (instead of the meta‐benzene), the anticancer drug vorinostat (instead of the phenyl ring), and the anesthetic drug benzocaine (instead of the para‐benzene). The patent‐free saturated analogs obtained showed a high potency in the corresponding biological assays.

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48

Prysiazhniuk, Kateryna, Oleksandr P. Datsenko, Oleksandr Polishchuk, Stanislav Shulha, Oleh Shablykin, Yelyzaveta Nikandrova, Kateryna Horbatok, et al. "Spiro[3.3]heptane as a Saturated Benzene Bioisostere**." Angewandte Chemie, January 22, 2024. http://dx.doi.org/10.1002/ange.202316557.

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Анотація:

AbstractThe spiro[3.3]heptane core, with the non‐coplanar exit vectors, was shown to be a saturated benzene bioisostere. This scaffold was incorporated into the anticancer drug sonidegib (instead of the meta‐benzene), the anticancer drug vorinostat (instead of the phenyl ring), and the anesthetic drug benzocaine (instead of the para‐benzene). The patent‐free saturated analogs obtained showed a high potency in the corresponding biological assays.

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49

Levterov, Vadym V., Yaroslav Panasiuk, Oleg Shablykin, Oleksandr Stashkevych, Kateryna Sahun, Artur Rassokhin, Iryna Sadkova, et al. "2‐Oxabicyclo[2.1.1]hexanes: Synthesis, Properties, and Validation as Bioisosteres of ortho‐ and meta‐Benzenes." Angewandte Chemie, March 11, 2024. http://dx.doi.org/10.1002/ange.202319831.

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Анотація:

We have developed a general and practical approach towards 2‑oxabicyclo[2.1.1]hexanes with two and three exit vectors via an iodocyclization reaction. The obtained compounds have been easily converted into the corresponding building blocks for use in medicinal chemistry. 2‑Oxabicyclo[2.1.1]hexanes have been incorporated into the structure of five drugs and three agrochemicals, and validated biologically as bioisosteres of ortho‐ and meta‐benzenes.

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50

Levterov, Vadym V., Yaroslav Panasiuk, Oleg Shablykin, Oleksandr Stashkevych, Kateryna Sahun, Artur Rassokhin, Iryna Sadkova, et al. "2‐Oxabicyclo[2.1.1]hexanes: Synthesis, Properties, and Validation as Bioisosteres of ortho‐ and meta‐Benzenes." Angewandte Chemie International Edition, March 11, 2024. http://dx.doi.org/10.1002/anie.202319831.

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Анотація:

We have developed a general and practical approach towards 2‑oxabicyclo[2.1.1]hexanes with two and three exit vectors via an iodocyclization reaction. The obtained compounds have been easily converted into the corresponding building blocks for use in medicinal chemistry. 2‑Oxabicyclo[2.1.1]hexanes have been incorporated into the structure of five drugs and three agrochemicals, and validated biologically as bioisosteres of ortho‐ and meta‐benzenes.

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