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Journal articles on the topic 'Aminobenzimidazoles'

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Author: Grafiati

Published: 10 December 2022

Last updated: 28 January 2023

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1

Zellmann, Felix, Laura Thomas, Ute Scheffer, Roland Hartmann, and Michael Göbel. "Site-Specific Cleavage of RNAs Derived from the PIM1 3′-UTR by a Metal-Free Artificial Ribonuclease." Molecules 24, no. 4 (February 23, 2019): 807. http://dx.doi.org/10.3390/molecules24040807.

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Oligonucleotide conjugates of tris(2-aminobenzimidazole) have been reported previously to cleave complementary RNA strands with high levels of sequence and site specificity. The RNA substrates used in these studies were oligonucleotides not longer than 29-mers. Here we show that ~150–400-mer model transcripts derived from the 3′-untranslated region of the PIM1 mRNA reacted with rates and specificities comparable to those of short oligonucleotide substrates. The replacement of DNA by DNA/LNA mixmers further increased the cleavage rate. Tris(2-aminobenzimidazoles) were designed to interact with phosphates and phosphate esters. A cell, however, contains large amounts of phosphorylated species that may cause competitive inhibition of RNA cleavage. It is thus important to note that no loss in reaction rates was observed in phosphate buffer. This opens the way to in-cell applications for this type of artificial nuclease. Furthermore, we disclose a new synthetic method giving access to tris(2-aminobenzimidazoles) in multigram amounts.

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2

Mumtaz, Mubeen, Nasir Rasool, Gulraiz Ahmad, Naveen Kosar, and Umer Rashid. "N-Arylation of Protected and Unprotected 5-Bromo-2-aminobenzimidazole as Organic Material: Non-Linear Optical (NLO) Properties and Structural Feature Determination through Computational Approach." Molecules 26, no. 22 (November 17, 2021): 6920. http://dx.doi.org/10.3390/molecules26226920.

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The interest in the NLO response of organic compounds is growing rapidly, due to the ease of synthesis, availability, and low loss. Here, in this study, Cu(II)-catalyzed selective N-arylation of 2-aminobenzimidazoles derivatives were achieved in the presence of different bases Et3N/TMEDA, solvents DCM/MeOH/H2O, and various aryl boronic acids under open atmospheric conditions. Two different copper-catalyzed pathways were selected for N-arylation in the presence of active nucleophilic sites, providing a unique tool for the preparation of NLO materials, C-NH (aryl) derivatives of 2-aminobenzimidazoles with protection and without protection of NH2 group. In addition to NMR analysis, all synthesized derivatives (1a–1f and 2a–2f) of 5-bromo-2-aminobenzimidazole (1) were computed for their non-linear optical (NLO) properties and reactivity descriptor parameters. Frontier molecular orbital (FMO) analysis was performed to get information about the electronic properties and reactivity of synthesized compounds.

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3

Danneberg, Friederike, Alice Ghidini, Plamena Dogandzhiyski, Elisabeth Kalden, Roger Strömberg, and Michael W. Göbel. "Sequence-specific RNA cleavage by PNA conjugates of the metal-free artificial ribonuclease tris(2-aminobenzimidazole)." Beilstein Journal of Organic Chemistry 11 (April 16, 2015): 493–98. http://dx.doi.org/10.3762/bjoc.11.55.

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Tris(2-aminobenzimidazole) conjugates with antisense oligonucleotides are effective site-specific RNA cleavers. Their mechanism of action is independent of metal ions. Here we investigate conjugates with peptide nucleic acids (PNA). RNA degradation occurs with similar rates and substrate specificities as in experiments with DNA conjugates we performed earlier. Although aggregation phenomena are observed in some cases, proper substrate recognition is not compromised. While our previous synthesis of 2-aminobenzimidazoles required an HgO induced cyclization step, a mercury free variant is described herein.

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4

Nájera, Carmen, José Miguel Sansano, and Enrique Gómez-Bengoa. "Heterocycle-based bifunctional organocatalysts in asymmetric synthesis." Pure and Applied Chemistry 88, no. 6 (June 1, 2016): 561–78. http://dx.doi.org/10.1515/pac-2016-0403.

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AbstractDifferent chiral bifunctional organocatalysts derived from trans-cyclohexane-1,2-diamine bearing different types of guanidine units able to form-hydrogen bonding activation have been designed. Conformational rigid 2-aminobenzimidazoles bearing a tertiary amino group have been used in enantioselective Michael type reactions of activated methylene compounds to nitroalkenes. The C2 symmetric bis(2-aminobenzimidazole) derivatives the appropriate organocatalyst for the conjugate addition of 1,3-dicarbonyl compounds to maleimides as well as for the SN1 reaction of benzylic alcohols with carbon nucleophiles. 2-Aminobenzimidazoles bearing a primary amino group have shown excellent catalytic activity in the Michael reaction of aldehydes to maleimides and nitroalkenes. Diastereomeric 2-aminopyrimidines bearing a prolinamide unit have been incorporated in the trans-cyclohexane-1,2-diamine scaffold and have been used for the inter- and intra-molecular direct aldol reaction under solvent-free conditions. For the Michael reaction of aldehydes with maleimides the primary amine 2-aminopyrimidine has shown excellent efficiency as organocatalyst. The bifunctional character of these organocatalysts has been demonstrated by means of DFT calculations.

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5

Milata, Viktor. "Nitro and aminobenzimidazoles." Acta Chimica Slovaca 11, no. 2 (October 1, 2018): 182–88. http://dx.doi.org/10.2478/acs-2018-0026.

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AbstractA summary of the preparation methods of 2 tautomeric and 4N-methylated benzimidazoles with a nitro group on the benzene ring (1–6) and with an amino group in the same positions (7–12) were summarized. Annular tautomerism of the title compounds1–12has been studied using1H,13C and15N NMR spectra in liquid and solid state (CPMAS), UV spectra and quantum chemical calculations.

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6

Gondal, Humaira Y., H. Mashooda, and Muhammad Ali. "New Antibacterial Peptide Analogs of 5-Aminobenzimidazoles." Journal of the Korean Chemical Society 55, no. 4 (August 20, 2011): 650–55. http://dx.doi.org/10.5012/jkcs.2011.55.4.650.

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7

Kumar, K. Anil, Prakash Kannaboina, D. Nageswar Rao, and Parthasarathi Das. "Nickel-catalyzed Chan–Lam cross-coupling: chemoselective N-arylation of 2-aminobenzimidazoles." Organic & Biomolecular Chemistry 14, no. 38 (2016): 8989–97. http://dx.doi.org/10.1039/c6ob01307d.

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8

Huang, Kuo-Ting, and Chung-Ming Sun. "Liquid-Phase combinatorial synthesis of aminobenzimidazoles." Bioorganic & Medicinal Chemistry Letters 12, no. 7 (April 2002): 1001–3. http://dx.doi.org/10.1016/s0960-894x(02)00091-4.

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9

Dyablo, O. V., A. F. Pozharskii, and N. N. Shkurupii. "Some properties of 1-(nitrophenyl)-aminobenzimidazoles." Chemistry of Heterocyclic Compounds 36, no. 1 (January 2000): 37–39. http://dx.doi.org/10.1007/bf02256841.

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10

Clark, Peter R., Glynn D. Williams, and Nicholas C. O. Tomkinson. "Copper-catalysed C–H functionalisation gives access to 2-aminobenzimidazoles." Organic & Biomolecular Chemistry 17, no. 34 (2019): 7943–55. http://dx.doi.org/10.1039/c9ob01651a.

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11

Chen, Jinjin, Zhaozhao Sun, Fuhong Xiao, and Guo-Jun Deng. "Base-promoted aerobic oxidative synthesis of fused 1,3,5-triazines under metal-free conditions." Green Chemistry 22, no. 20 (2020): 6778–82. http://dx.doi.org/10.1039/d0gc02691c.

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An efficient base-promoted aerobic oxidation procedure for the synthesis of fused 1,3,5-triazines from 2-aminobenzimidazoles, aromatic aldehydes, and ammonium iodide under metal-free conditions has been developed.

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12

Xie, Yuanyuan, Fan Zhang, Jianjun Li, and Xiangjun Shi. "Novel Synthesis of 2-Aminobenzimidazoles from Isoselenocyanates." Synlett 2010, no. 06 (February 17, 2010): 901–4. http://dx.doi.org/10.1055/s-0029-1219395.

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13

Hudson, Richard, David Fouchard, and L. Tillekeratne. "An Efficient One-Pot Synthesis of Aminobenzimidazoles." Synthesis 2005, no. 01 (November 17, 2004): 17–18. http://dx.doi.org/10.1055/s-2004-834925.

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14

Zhong, Min, Minna Bui, Wang Shen, Subramanian Baskaran, Darin A. Allen, Robert A. Elling, W. Michael Flanagan, et al. "2-Aminobenzimidazoles as potent Aurora kinase inhibitors." Bioorganic & Medicinal Chemistry Letters 19, no. 17 (September 2009): 5158–61. http://dx.doi.org/10.1016/j.bmcl.2009.07.016.

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15

Ueda, Satoshi, and Stephen L. Buchwald. "Catalyst-Controlled Chemoselective Arylation of 2-Aminobenzimidazoles." Angewandte Chemie International Edition 51, no. 41 (September 11, 2012): 10364–67. http://dx.doi.org/10.1002/anie.201204710.

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16

El kihel, A., M. El ouar, M. Ahbala, A. Mouzdahir, T. Harjane, and N. Knouzi. "Condensation of 5-aminobenzimidazoles with β-ketoester." Arabian Journal of Chemistry 3, no. 1 (January 2010): 9–12. http://dx.doi.org/10.1016/j.arabjc.2009.12.002.

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17

Ueda, Satoshi, and Stephen L. Buchwald. "Catalyst-Controlled Chemoselective Arylation of 2-Aminobenzimidazoles." Angewandte Chemie 124, no. 41 (September 11, 2012): 10510–13. http://dx.doi.org/10.1002/ange.201204710.

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18

Ho, Son, Pham Dao, and Chan Cho. "Microwave-Assisted Synthesis of Benzo[4,5]imidazo[1,2-a]pyrimidines from β-Bromo-α,β-unsaturated Aldehydes and 2-Aminobenzimidazoles." Synlett 28, no. 14 (May 12, 2017): 1811–15. http://dx.doi.org/10.1055/s-0036-1588834.

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β-Bromo-α,β-unsaturated aldehydes react with 2-aminobenzimidazoles by microwave irradiation in the presence of a base and magnesium sulfate to give the corresponding benzo[4,5]imidazo[1,2-a]pyrimidines in moderate to good yields.

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19

Kwak, Jung Pyo, Pham Duy Quang Dao, Nam Sik Yoon, and Chan Sik Cho. "Microwave-assisted green construction of imidazole-fused hybrid scaffolds using 2-aminobenzimidazoles as building blocks." RSC Advances 11, no. 35 (2021): 21367–74. http://dx.doi.org/10.1039/d1ra04396j.

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A green synthesis of trinuclear imidazole-fused hybrid scaffolds has been developed by transition metal-free double C(sp²)–N coupling and cyclization of 2-(2-bromoaryl)- and 2-(2-bromovinyl)imidazoles with 2-aminobenzimidazoles as building blocks under microwave irradiation.

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20

Cruz, Alejandro, Itzia I. Padilla Martínez, and Angel A. Ramos-Organillo. "Methods to Access 2-aminobenzimidazoles of Medicinal Importance." Current Organic Chemistry 23, no. 23 (January 9, 2020): 2573–97. http://dx.doi.org/10.2174/1385272823666191023150201.

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: Benzimidazole (BI) and derivatives are interesting because several of these compounds have been found to have a diversity of biological activities with clinical applications. In view of their importance, the synthesis of BI and its derivatives is still considered as a challenge for synthetic chemists. Examples of compounds used in medicinal chemistry containing BI, as important nucleus, are Astemizole (antihistaminic), Omeprazole (antiulcerative) and Rabendazole (fungicide), some of these compounds have the 2- aminobenzimidazole (2ABI) as base nucleus. The structure of 2ABI derivatives contains a cyclic guanidine moiety, which is interesting because of its free lone pairs, labile hydrogen atoms and planar delocalized structure. The delocalized 10-π electron system and the extension of the electron conjugation with the exocyclic amino group, in 2ABI, making these heterocycles to have amphoteric character. The 2ABI has been used as building blocks for the synthesis of several BI derivatives as medicinally important molecules. On these bases, herein, we present a bibliographic review concerning the recent methodologies used in the synthesis of 2ABIs, including the substituted ones.

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21

Dyablo, O. V., A. F. Fozharskii, and N. N. Shkurupii. "ChemInform Abstract: Some Properties of 1-(Nitrophenyl)aminobenzimidazoles." ChemInform 31, no. 43 (October 24, 2000): no. http://dx.doi.org/10.1002/chin.200043141.

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22

Cablewski, Teresa, Craig L. Francis, and Andris J. Liepa. "N, N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. V The Preparation of some Benzimidazo-Fused [1,2,4,6]Thiatriazine Dioxides." Australian Journal of Chemistry 61, no. 1 (2008): 59. http://dx.doi.org/10.1071/ch07336.

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N,N-dialkyl-N′-chlorosulfonyl chloroformamidines 1 were treated with 2-aminobenzimidazoles 2 to give [1,2,4,6]thiatriazino[2,3-a]benzimidazole 1,1-dioxides 3 and [1,2,4,6]thiatriazino[4,3-a]benzimidazole 2,2-dioxides 4. Some N-alkyl-, N-acyl-, and N-sulfonyl-derivatives of 3 were prepared. These products are derivatives of rare heterocycles.

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23

Rahimizadeh, Mohammad, Mehdi Pordel, Mehdi Bakavoli, Shima Rezaeian, and Hossein Eshghi. "Synthesis of a new heterocyclic system — Fluoreno[1,2-d]imidazol-10-one." Canadian Journal of Chemistry 87, no. 6 (June 2009): 724–28. http://dx.doi.org/10.1139/v09-062.

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Synthesis of various substituted fluoreno[1,2-d]imidazol-10-ones (5a–5g) has been accomplished by the cyclization of diazotized 1-substituted 4-benzoyl-5- aminobenzimidazoles (4a–4g). Compounds 4a–4g were prepared by reductive ring opening of 3H-imidazo[4′,5′:3,4]benzo[c]isoxazoles (3a–3g) with zinc dust in EtOH/NaOH solution.

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24

Nematpour, Manijeh, Elham Abedi, and Elahe Abedi. "A Novel One-pot Protocol for the Cu-Catalyzed Synthesis of Nine 2-Aminobenzimidazole Derivatives from o-Phenylenediamine and Trichloroacetonitrile." Letters in Organic Chemistry 16, no. 2 (January 9, 2019): 99–103. http://dx.doi.org/10.2174/1570178615666180914114010.

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The synthesis of a variety of 2-aminobenzimidazoles via a one pot reaction of ophenylenediamine and trichloroacetonitrile catalyzed by copper (II) acetate in THF at room temperature, with good yields is described. Use of simple and readily available starting materials, good to high yields, free ligand, and no column chromatography are important features of this protocol.

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25

Devine, Shane M., Matthew P. Challis, Jomo K. Kigotho, Ghizal Siddiqui, Amanda De Paoli, Christopher A. MacRaild, Vicky M. Avery, Darren J. Creek, Raymond S. Norton, and Peter J. Scammells. "Discovery and development of 2-aminobenzimidazoles as potent antimalarials." European Journal of Medicinal Chemistry 221 (October 2021): 113518. http://dx.doi.org/10.1016/j.ejmech.2021.113518.

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26

Ramachandran, Sreekanth, Shahul Hameed P., Abhishek Srivastava, Gajanan Shanbhag, Sapna Morayya, Nikhil Rautela, Disha Awasthy, et al. "N-Aryl-2-aminobenzimidazoles: Novel, Efficacious, Antimalarial Lead Compounds." Journal of Medicinal Chemistry 57, no. 15 (July 21, 2014): 6642–52. http://dx.doi.org/10.1021/jm500715u.

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27

Seth, Punit P., Dale E. Robinson, Elizabeth A. Jefferson, and Eric E. Swayze. "Efficient solution phase synthesis of 2-(N-acyl)-aminobenzimidazoles." Tetrahedron Letters 43, no. 41 (October 2002): 7303–6. http://dx.doi.org/10.1016/s0040-4039(02)01754-9.

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28

Xie, Yuanyuan, Fan Zhang, Jianjun Li, and Xiangjun Shi. "ChemInform Abstract: Novel Synthesis of 2-Aminobenzimidazoles from Isoselenocyanates." ChemInform 41, no. 31 (July 9, 2010): no. http://dx.doi.org/10.1002/chin.201031133.

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29

Popov, I. I., S. L. Boroshko, B. A. Tertov, and E. V. Tyukavina. "Condensation of 2-aminobenzimidazoles with o-substituted benzoyl chlorides." Chemistry of Heterocyclic Compounds 25, no. 2 (February 1989): 229. http://dx.doi.org/10.1007/bf00479928.

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30

Ueda, Satoshi, and Stephen L. Buchwald. "ChemInform Abstract: Catalyst-Controlled Chemoselective Arylation of 2-Aminobenzimidazoles." ChemInform 44, no. 12 (March 14, 2013): no. http://dx.doi.org/10.1002/chin.201312112.

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31

Bobošík, Vladimír, Viktor Milata, Dušan Ilavský, and Igor Goljer. "Synthesis and Cyclization of Some 5-Aminobenzimidazole and 5-Aminobenzotriazole Derivatives." Collection of Czechoslovak Chemical Communications 57, no. 2 (1992): 397–407. http://dx.doi.org/10.1135/cccc19920397.

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Alkoxymethylene derivatives I of 2,4-pentanedione, 3-oxobutanenitrile, and methyl and ethyl 3-oxobutanoates with substituted 1-phenyl-5-aminobenzimidazoles and -benzotriazoles II give the products of nucleophilic substitution III and IV which, bearing ester groups, undergo thermal cyclizations to the corresponding 8-acetyl-3-phenyl-6,9-dihydroazolo[4,5-f]quinolin-9(3H)-ones V and VI. IR, UV, 1H and 13C NMR data are given.

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32

Perusic-Janjic, Nada, Jevrem Janjic, and Sanja Podunavac-Kuzmanovic. "Solvent effect on electronic absorption spectra of some 2-aminobenzimidazoles." Acta Periodica Technologica, no. 33 (2002): 93–99. http://dx.doi.org/10.2298/apt0233093p.

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The effect of protic and aprotic solvents on electronic apsorption spectra of 1-(3-X-benzil)-2-aminobenzimidazoles (X=CH3;OCH3; Cl) was examined. UV-apsorption spectra (200-400 nm) were recorded in five protic and four aprotic solvents. Batochromic shift of absorption maxima, ?max, occurs from the solvent with the highest proton-donor ability to the proton acceptor solvent (from water to DMSO). Positions of absortion maxima in various solvents are in correlation with the dielectric constant of the solvent. In order to explain the obtained results, the ultraviolet absorption frequences of the electronic transitions of the compounds were correlated using a total solvatochromic equation of the form: ?max = ?0 + s?* + a? + b?, where??* is the measure of solvent polarity. Prepresents the scale of solvent hydrogen bond acceptor basicities and ? represents the scale of solvent hydrogen bond donor acidities. Correlation of spectroscopic data was carried out by means of multiple linear regression analysis.

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33

Li, Gang Liu, Zhanguo Wang, Yunyun Yuan, Chunxu Zhang, Hongyu Tian, Xianghong Wu, and Jing Zhang. "Multistep Parallel Synthesis of Substituted 5-Aminobenzimidazoles in Solution Phase." Journal of Combinatorial Chemistry 6, no. 5 (September 2004): 811–21. http://dx.doi.org/10.1021/cc049932f.

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34

Huggins, William M., T. Vu Nguyen, Nicholas A. Hahn, James T. Baker, Laura G. Kuo, Darpan Kaur, Roberta J. Melander, John S. Gunn, and Christian Melander. "2-Aminobenzimidazoles as antibiofilm agents against Salmonella enterica serovar Typhimurium." MedChemComm 9, no. 9 (2018): 1547–52. http://dx.doi.org/10.1039/c8md00298c.

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35

Nawrocka, Wanda, and Michał Zimecki. "Synthesis and Immunotropic Activity of Some 2-Aminobenzimidazoles, Part 4." Archiv der Pharmazie 331, no. 7-8 (July 1998): 249–53. http://dx.doi.org/10.1002/(sici)1521-4184(199807)331:7/8<249::aid-ardp249>3.0.co;2-b.

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36

Pozharskii, A. F., I. M. Nanavyan, V. V. Kuz'menko, A. I. Chernyshev, Yu V. Orlov, and N. A. Klyuev. "Oxidation of 1-aminobenzimidazoles. Synthesis and properties of 1,1?-azobenzimidazoles." Chemistry of Heterocyclic Compounds 25, no. 11 (November 1989): 1241–53. http://dx.doi.org/10.1007/bf00481518.

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37

Yu, Hui, Qiong Liu, Yuzhe Li, and Chongzhi Ni. "Copper-catalyzed synthesis of 2-aminobenzimidazoles from carbonimidoyl dichlorides and amines." Tetrahedron Letters 53, no. 39 (September 2012): 5253–56. http://dx.doi.org/10.1016/j.tetlet.2012.07.072.

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38

Su, Liqiang, Jing Feng, Ting Peng, Jinqiao Wan, Jing Fan, Jin Li, Jonathan O’Connell, David R. Lancia, G. Joseph Franklin, and Guansai Liu. "Synthesis of Multifunctional 2-Aminobenzimidazoles on DNA via Iodine-Promoted Cyclization." Organic Letters 22, no. 4 (January 30, 2020): 1290–94. http://dx.doi.org/10.1021/acs.orglett.9b04578.

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39

Gründemann, E., H. Graubaum, D. Martin, and E. Schiewald. "NMR investigations on benzheteroazoles. 2—NMR investigations ofN-acylated 2-aminobenzimidazoles." Magnetic Resonance in Chemistry 24, no. 1 (January 1986): 21–30. http://dx.doi.org/10.1002/mrc.1260240107.

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40

He, Xinhua, Sirish K. Lakkaraju, Marie Hanscom, Zaorui Zhao, Junfang Wu, Bogdan Stoica, Alexander D. MacKerell, Alan I. Faden, and Fengtian Xue. "Acyl-2-aminobenzimidazoles: A novel class of neuroprotective agents targeting mGluR5." Bioorganic & Medicinal Chemistry 23, no. 9 (May 2015): 2211–20. http://dx.doi.org/10.1016/j.bmc.2015.02.054.

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41

Guida, Xuan, Han Jianhua, and Li Xiaomin. "Synthesis and QSAR studies of novel 1-substituted-2-aminobenzimidazoles derivatives." European Journal of Medicinal Chemistry 41, no. 9 (September 2006): 1080–83. http://dx.doi.org/10.1016/j.ejmech.2006.01.002.

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42

Seth, Punit P., Dale E. Robinson, Elizabeth A. Jefferson, and Eric E. Swayze. "ChemInform Abstract: Efficient Solution Phase Synthesis of 2-(N-Acyl)-aminobenzimidazoles." ChemInform 33, no. 51 (May 18, 2010): no. http://dx.doi.org/10.1002/chin.200251136.

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43

Krchňák, Viktor, Jennifer Smith, and Josef Vágner. "Solid-Phase Traceless Synthesis of Selected Nitrogen-Containing Heterocyclic Compounds. The Encore Technique for Directed Sorting of Modular Solid Support." Collection of Czechoslovak Chemical Communications 66, no. 7 (2001): 1078–106. http://dx.doi.org/10.1135/cccc20011078.

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The acid lability of electron-rich N-benzylanilines has been exploited in a linker for the traceless solid-phase synthesis of benzimidazoles, 2-aminobenzimidazoles, quinoxalinones and tetrahydroquinoxalines. The target compound precursors were assembled on a solid-phase support derivatized with either a benzylamine or a benzhydrylamine linker. Exposure to an acidic reagent caused cleavage of the C(benzyl)-N(aniline) bond, releasing the product with only a hydrogen atom on the descending nitrogen. The Encore technique for directed sorting on SynPhase Lanterns has been developed and applied to combinatorial synthesis of generic drug discovery libraries.

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44

Ferreira, Rafael Augusto Alves, Celso de Oliveira Rezende Junior, Pablo David Grigol Martinez, Paul John Koovits, Bruna Miranda Soares, Leonardo L. G. Ferreira, Simone Michelan-Duarte, et al. "2-aminobenzimidazoles for leishmaniasis: From initial hit discovery to in vivo profiling." PLOS Neglected Tropical Diseases 15, no. 2 (February 22, 2021): e0009196. http://dx.doi.org/10.1371/journal.pntd.0009196.

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Leishmaniasis is a major infectious disease with hundreds of thousands of new cases and over 20,000 deaths each year. The current drugs to treat this life-threatening infection have several drawbacks such as toxicity and long treatment regimens. A library of 1.8 million compounds, from which the hits reported here are publicly available, was screened against Leishmania infantum as part of an optimization program; a compound was found with a 2-aminobenzimidazole functionality presenting moderate potency, low metabolic stability and high lipophilicity. Several rounds of synthesis were performed to incorporate chemical groups capable of reducing lipophilicity and clearance, leading to the identification of compounds that are active against different parasite strains and have improved in vitro properties. As a result of this optimization program, a group of compounds was further tested in anticipation of in vivo evaluation. In vivo tests were carried out with compounds 29 (L. infantum IC50: 4.1 μM) and 39 (L. infantum IC50: 0.5 μM) in an acute L. infantum VL mouse model, which showed problems of poor exposure and lack of efficacy, despite the good in vitro potency.

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45

Phakhodee, Wong, Chuthamat Duangkamol, Nittaya Wiriya, and Mookda Pattarawarapan. "Ultrasound-assisted synthesis of substituted 2-aminobenzimidazoles, 2-aminobenzoxazoles, and related heterocycles." Tetrahedron Letters 57, no. 47 (November 2016): 5290–93. http://dx.doi.org/10.1016/j.tetlet.2016.10.060.

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Xie, Yangxi, Luoyuan Li, Shaofa Sun, Zijun Wu, Ming Lang, Di Jiang, and Jian Wang. "Enantioselective NHC-Catalyzed [3+3] Annulation of α-Bromoenals with 2-Aminobenzimidazoles." Organic Letters 22, no. 2 (January 8, 2020): 391–94. http://dx.doi.org/10.1021/acs.orglett.9b04054.

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Ding, Kejia, Annie Wang, Mark A. Boerneke, Sergey M. Dibrov, and Thomas Hermann. "Aryl-substituted aminobenzimidazoles targeting the hepatitis C virus internal ribosome entry site." Bioorganic & Medicinal Chemistry Letters 24, no. 14 (July 2014): 3113–17. http://dx.doi.org/10.1016/j.bmcl.2014.05.009.

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NAWROCKA, W., and M. ZIMECKI. "ChemInform Abstract: Synthesis and Immunotropic Activity of Some 2-Aminobenzimidazoles. Part 4." ChemInform 29, no. 50 (June 18, 2010): no. http://dx.doi.org/10.1002/chin.199850177.

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Kihel, Abdellatif El, Mohamed Benchidmi, El Mokhtar Essassi, Patrick Bauchat, and Renee Danion-bougot. "Reaction of Aminobenzimidazoles with 4-Hydroxy-6-methyl-2-pyrone and 4-Hydroxycoumarine." Synthetic Communications 29, no. 14 (July 1999): 2435–45. http://dx.doi.org/10.1080/00397919908086250.

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Artman, Gerald D., Catherine F. Solovay, Christopher M. Adams, Brian Diaz, Martin Dimitroff, Takeru Ehara, Danlin Gu, et al. "One-pot synthesis of 2-aminobenzimidazoles using 2-chloro-1,3-dimethylimidazolinium chloride (DMC)." Tetrahedron Letters 51, no. 40 (October 2010): 5319–21. http://dx.doi.org/10.1016/j.tetlet.2010.07.177.

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