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Journal articles on the topic 'Benzamidine analogues'

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Published: 10 December 2022

Last updated: 28 January 2023

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1

Fouda, A. S., M. A. Ismail, A. S. Abousalem, and G. Y. Elewady. "Experimental and theoretical studies on corrosion inhibition of 4-amidinophenyl-2,2′-bifuran and its analogues in acidic media." RSC Adv. 7, no. 73 (2017): 46414–30. http://dx.doi.org/10.1039/c7ra08092a.

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Corrosion inhibition studies of carbon steel (CS) in 1 M HCl by newly synthesized bichalcophene compounds namely; 4-(2,2′-bifuran-5-yl)benzamidine (MA-0947) and 6-(2,2′-bifuran-5-yl)nicotinamidine (MA-0941) and 6-[5-(thiophen-2-yl)furan-2-yl]nicotinamidine (MA-0940).

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2

Sa’ad, Mohammad Auwal, Ramasamy Kavitha, Shivkanya Fuloria, Neeraj Kumar Fuloria, Manickam Ravichandran, and Pattabhiraman Lalitha. "Synthesis, Characterization and Biological Evaluation of Novel Benzamidine Derivatives: Newer Antibiotics for Periodontitis Treatment." Antibiotics 11, no. 2 (February 7, 2022): 207. http://dx.doi.org/10.3390/antibiotics11020207.

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Periodontal disease (PD) is complex polymicrobial disease which destroys tooth-supporting tissue. Although various synthetic inhibitors of periodontitis-triggering pathogens have been recognized, their undesirable side effects limit their application. Hence, the present study intended to perform the synthesis, characterization, antimicrobial evaluation, and cytotoxicity analysis of novel benzamidine analogues (NBA). This study involved the synthesis of novel imino bases of benzamidine (4a–c), by reacting different aromatic aldehydes with 2-(4-carbamimidoylphenoxy) acetohydrazide (3), which was synthesized by the hydrazination of ethyl 2-(4-carbamimidoylphenoxy) acetate (2), the derivative of 4-hydroxybenzene carboximidamide (1). This was followed by characterization using FTIR, 1H, 13C NMR and mass spectrometry. All synthesized compounds were further tested for antimicrobial potential against PD-triggering pathogens by the micro broth dilution method. The cytotoxicity analysis of the NBA against HEK 293 cells was conducted using an MTT assay. The present study resulted in a successful synthesis of NBA and elucidated their structures. The synthesized NBA exhibited significant antimicrobial activity values between 31.25 and 125 µg/mL against tested pathogens. All NBA exhibited weak cytotoxicity against HEK 293 cells at 7.81 µg, equally to chlorhexidine at 0.2%. The significant antimicrobial activity of NBA against PD-triggering pathogens supports their potential application in periodontitis treatment.

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3

Atassi, M. Z. "Surface-simulation synthesis of the substrate-binding site of an enzyme. Demonstration with trypsin." Biochemical Journal 226, no. 2 (March 1, 1985): 477–85. http://dx.doi.org/10.1042/bj2260477.

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From the X-ray co-ordinates of bovine trypsin and its complexes with substrate analogues (benzamidine) and with soya-bean trypsin inhibitor, a peptide (TP) was designed and synthesized by surface-simulation synthesis, a concept previously introduced by this laboratory, to mimic the binding site of trypsin. Also, a control peptide (CTP) was synthesized that contained all the amino acids present in the TP peptide, except that their order was randomized. The radioiodinated TP peptide bound specifically to adsorbents of benzamidine, whereas the control CTP peptide exhibited no binding activity. Conjugates to succinyl (3-carboxypropionyl)-lysozyme of the TP peptide, control CTP peptide and other unrelated peptides were examined by a radiometric binding assay for the ability to bind soya-bean trypsin inhibitor and human alpha 1-antitrypsin. Conjugates of the TP peptide exhibited considerable binding activity to adsorbents of soya-bean trypsin inhibitor or alpha 1-antitrypsin. None of the other peptide conjugates possessed any binding activity. Action of the active-site-directed reagents phenylmethanesulphonyl fluoride and di-isopropyl phosphorofluoridate on free TP and CTP peptides resulted in the modification of a serine residue in the TP peptide whereas the CTP peptide remained unaltered. The TP peptide, either in the free form or as a conjugate on succinyl-lysozyme, had no enzymic activity on protein substrates or on tosylarginine methyl ester. These findings indicated that the binding activity of an enzyme was well mimicked by the surface-stimulation peptide but that reproduction of the catalytic activity was not obtained.

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4

Kalinichenko, Elena, Aliaksandr Faryna, Viktoria Kondrateva, Alena Vlasova, Valentina Shevchenko, Alla Melnik, Olga Avdoshko, and Alla Belko. "Synthesis, Biological Activities and Docking Studies of Novel 4-(Arylaminomethyl)benzamide Derivatives as Potential Tyrosine Kinase Inhibitors." Molecules 24, no. 19 (September 30, 2019): 3543. http://dx.doi.org/10.3390/molecules24193543.

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A number of new compounds containing the 4-(aminomethyl)benzamide fragment as a linker were designed and synthesized, and their biological activities were evaluated as potential anticancer agents. The cytotoxicity activity of the designed compounds was studied in two hematological and five solid cell lines in comparison with the reference drugs. Targeted structures against eight receptor tyrosine kinases including EGFR, HER-2, HER-4, IGF1R, InsR, KDR, PDGFRa, and PDGFRb were investigated. The majority of the compounds showed a potent inhibitory activity against the tested kinases. The analogues 11 and 13 with the (trifluoromethyl)benzene ring in the amide or amine moiety of the molecule were proven to be highly potent against EGFR, with 91% and 92% inhibition at 10 nM, respectively. The docking of synthesized target compounds for nine protein kinases contained in the Protein Data Bank (PDB) database was carried out. The molecular modeling results for analogue 10 showed that the use of the 4-(aminomethyl)benzamide as a flexible linker leads to a favorable overall geometry of the molecule, which allows one to bypass the bulk isoleucine residue and provides the necessary binding to the active center of the T315I-mutant Abl (PDB: 3QRJ).

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5

Veselinović, Aleksandar M., Andrey Toropov, Alla Toropova, Dobrila Stanković-Đorđević, and Jovana B. Veselinović. "Design and development of novel antibiotics based on FtsZ inhibition – in silico studies." New Journal of Chemistry 42, no. 13 (2018): 10976–82. http://dx.doi.org/10.1039/c8nj01034j.

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6

Sugano, Kiyohiko, Shoshin Yoshida, Mikio Takaku, Masayuki Haramura, Ryoichi Saitoh, Yoshiaki Nabuchi, and Hidetoshi Ushio. "Quantitative structure–intestinal permeability relationship of benzamidine analogue thrombin inhibitor." Bioorganic & Medicinal Chemistry Letters 10, no. 17 (September 2000): 1939–42. http://dx.doi.org/10.1016/s0960-894x(00)00367-x.

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7

Elkamhawy, Ahmed, Na Kyoung Oh, Noha A. Gouda, Magda H. Abdellattif, Saud O. Alshammari, Mohammed A. S. Abourehab, Qamar A. Alshammari, et al. "Novel Hybrid Indole-Based Caffeic Acid Amide Derivatives as Potent Free Radical Scavenging Agents: Rational Design, Synthesis, Spectroscopic Characterization, In Silico and In Vitro Investigations." Metabolites 13, no. 2 (January 17, 2023): 141. http://dx.doi.org/10.3390/metabo13020141.

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Antioxidant small molecules can prevent or delay the oxidative damage caused by free radicals. Herein, a structure-based hybridization of two natural antioxidants (caffeic acid and melatonin) afforded a novel hybrid series of indole-based amide analogues which was synthesized with potential antioxidant properties. A multiple-step scheme of in vitro radical scavenging assays was carried out to evaluate the antioxidant activity of the synthesized compounds. The results of the DPPH assay demonstrated that the indole-based caffeic acid amides are more active free radical scavenging agents than their benzamide analogues. Compared to Trolox, a water-soluble analogue of vitamin E, compounds 3a, 3f, 3h, 3j, and 3m were found to have excellent DPPH radical scavenging activities with IC50 values of 95.81 ± 1.01, 136.8 ± 1.04, 86.77 ± 1.03, 50.98 ± 1.05, and 67.64 ± 1.02 µM. Three compounds out of five (3f, 3j, and 3m) showed a higher capacity to neutralize the radical cation ABTS•+ more than Trolox with IC50 values of 14.48 ± 0.68, 19.49 ± 0.54, and 14.92 ± 0.30 µM, respectively. Compound 3j presented the highest antioxidant activity with a FRAP value of 4774.37 ± 137.20 μM Trolox eq/mM sample. In a similar way to the FRAP assay, the best antioxidant activity against the peroxyl radicals was demonstrated by compound 3j (10,714.21 ± 817.76 μM Trolox eq/mM sample). Taken together, compound 3j was validated as a lead hybrid molecule that could be optimized to maximize its antioxidant potency for the treatment of oxidative stress-related diseases.

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8

Balkrishna, Shah Jaimin, Shailesh Kumar, Gajendra Kumar Azad, Bhagat Singh Bhakuni, Piyush Panini, Navjeet Ahalawat, Raghuvir Singh Tomar, Michael R. Detty, and Sangit Kumar. "An ebselen like catalyst with enhanced GPx activity via a selenol intermediate." Org. Biomol. Chem. 12, no. 8 (2014): 1215–19. http://dx.doi.org/10.1039/c4ob00027g.

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Benzamide ring-substituted, quinine-derived ebselen analogue is synthesized which exists in selenol form upon addition of PhSH. It catalyses oxidation of PhSH with H₂O₂ faster (10³-fold) than ebselen.

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9

Ong, Xandria, Manan Ahmed, Luonan Xu, Ashley T. Brennan, Carol Hua, Katrina A. Zenere, Zixi Xie, Cameron J. Kepert, Benjamin J. Powell, and Suzanne M. Neville. "Spin-Crossover 2-D Hofmann Frameworks Incorporating an Amide-Functionalized Ligand: N-(pyridin-4-yl)benzamide." Chemistry 3, no. 1 (March 1, 2021): 360–72. http://dx.doi.org/10.3390/chemistry3010026.

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Two analogous 2-D Hofmann-type frameworks, which incorporate the novel ligand N-(pyridin-4-yl)benzamide (benpy) [FeII(benpy)2M(CN)4]·2H2O (M = Pd (Pd(benpy)) and Pt (Pt(benpy))) are reported. The benpy ligand was explored to facilitate spin-crossover (SCO) cooperativity via amide group hydrogen bonding. Structural analyses of the 2-D Hofmann frameworks revealed benpy-guest hydrogen bonding and benpy-benpy aromatic contacts. Both analogues exhibited single-step hysteretic spin-crossover (SCO) transitions, with the metal-cyanide linker (M = Pd or Pt) impacting the SCO spin-state transition temperature and hysteresis loop width (Pd(benpy): T½↓↑: 201, 218 K, ∆T: 17 K and Pt(benpy): T½↓↑: 206, 226 K, ∆T: 20 K). The parallel structural and SCO changes over the high-spin to low-spin transition were investigated using variable-temperature, single-crystal, and powder X-ray diffraction, Raman spectroscopy, and differential scanning calorimetry. These studies indicated that the ligand–guest interactions facilitated by the amide group acted to support the cooperative spin-state transitions displayed by these two Hofmann-type frameworks, providing further insight into cooperativity and structure–property relationships.

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10

Sugano, Kiyohiko, Shoshin Yoshida, Mikio Takaku, Masayuki Haramura, Ryoichi Saitoh, Yoshiaki Nabuchi, and Hidetoshi Ushio. "Corrigendum to “Quantitative structure–Intestinal permeability relationship of benzamidine analogue thrombin inhibitor”." Bioorganic & Medicinal Chemistry Letters 11, no. 8 (April 2001): 1097. http://dx.doi.org/10.1016/s0960-894x(01)00121-4.

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11

Mondal, Pradip Kumar, Rahul Shukla, Subha Biswas, and Deepak Chopra. "Role of halogen-involved intermolecular interactions and existence of isostructurality in the crystal packing of —CF3 and halogen (Cl or Br or I) substituted benzamides." Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials 74, no. 6 (November 14, 2018): 574–91. http://dx.doi.org/10.1107/s2052520618013422.

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A total of 23 benzamides are obtained through a simple reaction between chloro-/bromo-/iodoaniline and trifluoromethylbenzoyl chloride and characterized using single-crystal X-ray diffraction. Crystal structures of three series of benzamides based on N-chlorophenyl–trifluoromethyl–benzamide (nine compounds), N-bromophenyl–trifluoromethyl–benzamide (six compounds), and N-iodophenyl–trifluoromethyl–benzamide (eight compounds) are prepared to analyse the halogen-mediated noncovalent interactions. The influences of Cl/Br/I and trifluoromethyl substituents on the respective interactions are examined in the presence of a strong N—H...O hydrogen bond. This exercise has resulted in the documentation of frequently occurring supramolecular synthons involving halogen atoms in the crystal packing of benzamide molecules in the solid state. In the present study, a detailed quantitative evaluation has been performed on the nature, energetics, electrostatic contributions, and topological properties of short and directional intermolecular interactions derived from the electron density on halogenated benzamides in the solid state. Besides these, the occurrence of three-, two- and one-dimensional isostructurality in halogen (Cl or Br or I) substituted benzamide analogues is also investigated. A `region of co-existence' involving halogen-based intermolecular interactions in the vicinity of the sum of the van der Waals radii has been identified. Thus, the nature of the halogen (effective size), type of interaction and the packing characteristics via presence of additional interactions establish the subtle, yet important, role of cooperativity in intermolecular interactions in crystal packing.

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12

Slavíková, Barbora, Alexander Kasal, and Ladislav Kohout. "N-Benzoyl-N-methylandrostan-17β-amines; 20-Aza Analogues of Brassinolide." Collection of Czechoslovak Chemical Communications 63, no. 5 (1998): 655–61. http://dx.doi.org/10.1135/cccc19980655.

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3β-Hydroxyandrost-5-en-17-one (1) was converted into 17β-(N-methylamino)androst-5-en-3β-ol (4). In the corresponding N-benzamide 5, structural features characteristic of brassinolide were produced in a standard way, i.e. via 3α,5α-cyclo derivatives 7 and 8, ∆2-olefin 9 and 2α,3α-diol 10. Baeyer-Villiger oxidation yielded two products: 2α,3α-dihydroxy-17β-N-(methylbenzamido)-7-oxa-7a-homo-5α-androstan-6-one (11) and 2α,3α-dihydroxy-17β-(N-methylbenzamido)-6-oxa-7a-homo-5α-androstan-7-one (12).

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13

Collin, Sonia, Florence Moureau, Mirna Gil Quintero, Daniel P. Vercauteren, Guy Evrard, and Fran�ois Durant. "Stereoelectronic requirements of benzamide 5HT3 antagonists. Comparison with D2 antidopaminergic analogues." Journal of the Chemical Society, Perkin Transactions 2, no. 1 (1995): 77. http://dx.doi.org/10.1039/p29950000077.

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14

Mach, Robert H., Yunsheng Huang, Rebekah A. Freeman, Li Wu, Suwanna Vangveravong, and Robert R. Luedtke. "Conformationally-flexible benzamide analogues as dopamine D3 and σ2 receptor ligands." Bioorganic & Medicinal Chemistry Letters 14, no. 1 (January 2004): 195–202. http://dx.doi.org/10.1016/j.bmcl.2003.09.083.

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15

Mariani, Alberto, Sabina L. E. Mazzanti, and Saverio Russo. "Role of the reaction parameters in the direct synthesis of aromatic polyamides." Canadian Journal of Chemistry 73, no. 11 (November 1, 1995): 1960–65. http://dx.doi.org/10.1139/v95-242.

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A thorough study, devoted to analyzing the role of various reaction parameters in the direct synthesis of poly(p-phenylene terephthalamide) and poly(p-benzamide), activated by triphenyl phosphite, is described. The effects of temperature, salt type and concentration, amount of triphenyl phosphite and its stepwise introduction, as well as monomer and reagent concentrations, are considered. The inherent viscosity values of the above aromatic polyamides are higher than those reported in the literature for analogous syntheses and are comparable to the values of typical samples obtained by the acyl chloride routes. Keywords: poly(p-benzamide), poly(p-phenylene terephthalamide), triphenylphosphite, direct synthesis, aromatic polyamides.

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16

Li, Jin, Qinggang Meng, Yang Lei, Bing Gu, Yu Liu, and Weiyue Lu. "Benzamide analogue-conjugated polyethylenimine for brain-targeting and gene delivery." Journal of Drug Targeting 19, no. 9 (October 14, 2011): 814–20. http://dx.doi.org/10.3109/1061186x.2011.572975.

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17

Brown, J. M., M. J. Lemmon, M. R. Horsman, and W. W. Lee. "Structure–activity Relationships for Tumour Radiosensitization by Analogues of Nicotinamide and Benzamide." International Journal of Radiation Biology 59, no. 3 (January 1991): 739–48. http://dx.doi.org/10.1080/09553009114550651.

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18

Nader, M. A., K. L. Green, R. R. Luedtke, and R. H. Mach. "The effects of benzamide analogues on cocaine self-administration in rhesus monkeys." Psychopharmacology 147, no. 2 (November 19, 1999): 143–52. http://dx.doi.org/10.1007/s002130051154.

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19

Hatano, Kentaro, Tastuo Ido, Kiichi Ishiwata, Koichiro Kawashiroa, Jun Hatazawa, Masatoshi Itoh, and Ren Iwata. "Synthesis of [18F]fluoroalkylated analogues of a benzamide nuroleptic; YM-09151-2." Journal of Labelled Compounds and Radiopharmaceuticals 26, no. 1-12 (January 1989): 329–31. http://dx.doi.org/10.1002/jlcr.25802601142.

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20

Horsman, MR, and DJ Chaplin. "Enhancement of cyclophosphamide cytotoxicity in vivo by the benzamide analogue pyrazinamide." British Journal of Cancer 69, no. 4 (April 1994): 648–54. http://dx.doi.org/10.1038/bjc.1994.126.

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21

Zhang, Qing-Wei, and Jian-Qi Li. "Synthesis and Biological Evaluation of N-(Aminopyridine) Benzamide Analogues as Histone Deacetylase Inhibitors." Bulletin of the Korean Chemical Society 33, no. 2 (February 20, 2012): 535–40. http://dx.doi.org/10.5012/bkcs.2012.33.2.535.

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22

Jørgensen, Charlotte G., Bente Frølund, Jan Kehler, and Anders A. Jensen. "Discovery of Benzamide Analogues as a Novel Class of 5-HT3 Receptor Agonists." ChemMedChem 6, no. 4 (January 18, 2011): 725–36. http://dx.doi.org/10.1002/cmdc.201000444.

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23

Janabi, Mustafa, Catherine M. Pollock, Ann-Marie Chacko, and Duncan H. Hunter. "Resin-supported arylstannanes as precursors for radiolabeling with iodine: benzaldehydes, benzoic acids, benzamides, and NHS esters." Canadian Journal of Chemistry 93, no. 2 (February 2015): 207–17. http://dx.doi.org/10.1139/cjc-2014-0265.

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A highly cross-linked polystyrene resin bearing a reactive chlorostannane moiety 1 has been used to generate a variety of arylstannane radiopharmaceutical precursors for no-carrier-added radioiodination. The resins were characterized for their solvent compatibility and sensitivity to acid cleavage. Resin-supported arylstannanes synthesized via their aryllithium analogues include 3- and 4-stannylbenzaldehydes, 3- and 4-stannylbenzoic acids, and 3- and 4-N-succinimidyl benzoates. A three-step route to the resin-supported stannylbenzoic acids 12a/b was developed through resin-supported benzaldehydes 11a/b. The aldehyde to acid conversion efficiency is >90%, and acid loading capacities of 0.66–0.94 mmol/g were obtained. Resin-supported N-succinimidyl benzoates 16a/b were prepared from the acid with 78%–84% conversion efficiency. Libraries of resin-supported benzamides 19a/b prepared from amine conjugation to corresponding benzoic acids or N-succinimidyl benzoates are described. A third approach describes the preparation of resin-supported benzamides via direct conjugation of the dilithio salt of the intact benzamide to the chlorostannane resin 1. Lastly, as proof-of-principle, a radiolabeling study with iodine-131 (131I) was performed with a resin-supported benzamide to afford the corresponding radioligand in moderate yields, and high radiochemical purity.

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24

Chaplin, DJ, MJ Trotter, KA Skov, and MR Horsman. "Modification of tumour radiation response in vivo by the benzamide analogue pyrazinamide." British Journal of Cancer 62, no. 4 (October 1990): 561–66. http://dx.doi.org/10.1038/bjc.1990.330.

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25

Šmidrkal, Jan, Jiří Holubek, and Jan Trojánek. "The synthesis of 2,3,7,8-bismethylenedioxy-11-methoxy-5-methylbenzo[c]phenanthridinium chloride." Collection of Czechoslovak Chemical Communications 50, no. 4 (1985): 984–90. http://dx.doi.org/10.1135/cccc19850984.

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Acylation of 3-methoxy-6,7-methylenedioxy-l-methylaminonaphthalene (VI) with 6-bromo-2,3-methylenedioxybenzoyl chloride gave N-(3-methoxy-6,7-methylenedioxynaphth-l-yl)-N-methylamide of 6-bromo-2,3-methylenedioxybenzoic acid (IIIa) the irradiation of which with ultraviolet light in acetonitrile and triethylamine gave N-methyl-2,3-methylenedioxy-l-(3'-methoxy-6',7'-methylenedioxynaphth-l-yl)benzamide (Xa) in low yield in addition to 2,3,7,8-bismethylenedioxy-11-methoxy-5-methyl-6-oxobenzo(c)phenanthridine (Va). The last compound was converted to dihydro derivative VIa from which 2,3,7,8-bismethylenedioxy-11-methoxy-5-methylbenzo[c]-phenanthridinium chloride (Ia) was prepared. Chloride Ia differs from the alkaloid chelirubine (IIa) to which the structure Ia was assigned originally. Under analogous conditions irradiation of N-(3-methoxy-6,7-methylenedioxynaphth-l-yl)-N-methylamide of 6-bromo-2,3-dimethoxybenzoic acid (IIIb) leads to debrominated starting amide XIIIb on the one hand and to N-methyl-2,3-dimethoxy-l-(3'-methoxy-6',7'-methylenedioxynaphth-l-yl)benzamide (Xb) on the other. The expected phenanthridone derivative Vb could not be detected in the reaction mixture.

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26

Ahsan, Mohamed Jawed, Rupesh Kumar Kumawat, Surender Singh Jadav, Mohammed H. Geesi, Mohammed Afroz Bakht, Mohd Zaheen Hassan, Abdulmalik Bin Saleh Al-Tamimi, et al. "Synthesis, Cytotoxic Evaluation, and Molecular Docking Studies of N-(7- hydroxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetamide/benzamide Analogues." Letters in Drug Design & Discovery 16, no. 2 (November 29, 2018): 182–93. http://dx.doi.org/10.2174/1570180815666180501160047.

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Background: Cancer caused nearly 8.8 million deaths in 2015. Limited efficacy, selectivity, drug resistance and toxicity are major complications associated with chemotherapy, potentiating the discovery of anticancer agents. Methods: A new series of N-(7-hydroxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetamide/benzamide analogues (5a-j) was prepared from the precursor, 7-hydroxy-4-methyl-2H-chromen-2-one (3), as anticancer agent. The structural assignment of quinolone analogues (5a-j) was based on spectroscopic data analyses. The cytotoxicity was tested on breast cancer cell lines (MCF7 and MDA-MB- 231) by sulforhodamine B (SRB) assay and three dose-related parameters GI50, TGI, and LC50 were calculated. Results: 2-(2-chlorophenoxy)-N-(7-hydroxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetamide (5a) showed the most potent cytotoxicity against the MCF7 and MDA-MB-231 cancer cell lines with GI50 of 18.7 and 48.1 µM respectively. The glide scores of the compounds, 5a-d were found to be related to the cytotoxicity profile and the emodel scores for ligands, 5a-j were found to be related to significant cytotoxicity. Conclusion: Compound 5a exhibited the most potent cytotoxicity and this report may provide some predictions to design more potent novel quinolines as cytotoxic agents.

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27

Collin, Sonia, Daniel P. Vercauteren, Guy Evrard, and Fran�ois Durant. "Molecular structure analysis of benzamide neuroleptics. Part 13. A tropapride sulphonamidic analogue C15H22N3O3SCl." Journal of the Chemical Society, Perkin Transactions 2, no. 5 (1989): 407. http://dx.doi.org/10.1039/p29890000407.

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28

Elaut, G., G. Laus, P. Papeleu, V. Breckx, J. Van Hemel, M. Erra, G. Brosch, et al. "284 Benzamide-based trichostatin a analogues are potent and metabolically stable inhibitors of histone deacetylase." Toxicology Letters 144 (September 2003): s78. http://dx.doi.org/10.1016/s0378-4274(03)90283-9.

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29

Sestili, P., C. Balsmini, G. Spadoni, F. Cattabeni, and O. Cantoni. "Analogues of benzamide as poly(ADP-ribose)transferase inhibitors: A study on structure activity relationships." Pharmacological Research Communications 20, no. 7 (July 1988): 613–14. http://dx.doi.org/10.1016/s0031-6989(88)80091-2.

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30

Batool, Farhana, Maria A. Khan, Nimra N. Shaikh, Shazia Iqbal, Shahida Akbar, Saba Fazal‐ur‐rehman, Muhammad Iqbal Choudhary, and Fatima Z. Basha. "New Benzamide Analogues of Metronidazole‐tethered Triazoles as Non‐sugar Based Inhibitors of β ‐Glucuronidase." ChemistrySelect 4, no. 29 (August 5, 2019): 8634–37. http://dx.doi.org/10.1002/slct.201901870.

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31

Wadhwa, Pankaj, Priti Jain, Arpit Patel, Shantanu Shinde, and Hemant R. Jadhav. "Synthesis and Evaluation of 3-(1,3-dioxoisoindolin-2-yl)-N-substituted Phenyl Benzamide Analogues as HIV Integrase Strand Transfer Inhibitors." Anti-Infective Agents 17, no. 2 (July 5, 2019): 105–14. http://dx.doi.org/10.2174/2211352516666181102121920.

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<P>Background: A series of novel 3-(1,3-dioxoisoindolin-2-yl)-N-substituted phenyl benzamide derivatives was synthesized and tested in vitro against human immunodeficiency virus type-1 Integrase (HIV-1 IN). Methods: Out of the 18 analogues, six (compounds 16c, 16h, 16i, 16m, 16n and 16r) showed significant inhibition of strand transfer by HIV-1 integrase. For these six compounds. IC50 was below 5.0 µM. In silico docking studies revealed that the presence of 2-phenyl isoindoline-1,3-dione motif was essential as it was found to interact with active site magnesium. Results: To further confirm the results, cell-based HIV-1 and HIV-2 inhibitory assay was carried out. Conclusion: These compounds possess structural features not seen in previously reported HIV-1 integrase inhibitors and thus can help further optimization of anti-HIV-1 integrase activity.</P>

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32

Pankiewicz, Krzysztof W., and Krzysztof Felczak. "From ribavirin to NAD analogues and back to ribavirin in search for anticancer agents." Heterocyclic Communications 21, no. 5 (October 1, 2015): 249–57. http://dx.doi.org/10.1515/hc-2015-0133.

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AbstractRibavirin, a broad-spectrum antiviral agent is used in the clinic alone or in combination with other antivirals and/or interferons. Numerous structural analogues of ribavirin have been developed, among them tiazofurin, which is inactive against viruses but is a potent anticancer drug. Tiazofurin was found to inhibit nicotinamide adenine dinucleotide (NAD)-dependent inosine monophosphate dehydrogenase (IMPDH) after metabolic conversion into tiazofurin adenine dinucleotide (TAD), which binds well but could not serve as IMPDH cofactor. TAD showed high selectivity against human IMPDH vs. other cellular dehydrogenases. Mycophenolic acid (MPA) was even more specific, binding at the cofactor-binding domain of IMPDH. Ribavirin adenine dinucleotide, however, did not show any significant inhibition at the enzymatic level. We synthesized numerous NAD analogues in which natural nicotinamide riboside was replaced by tiazofurin, MPA moiety, or benzamide riboside, and the adenosine moiety as well as the pyrophosphate linker were broadly modified. Some of these compounds were found to be low nanomolar inhibitors of the enzyme and sub-micromolar inhibitors of cancer cell line proliferation. The best were as potent as tyrosine kinase inhibitor gleevec heralded as a ‘magic bullet’ against chronic myelogenous leukemia. In recent years, ribavirin was rediscovered as a potential anticancer agent against number of tumors including leukemia. It was clearly established that its antitumor activity is related to the inhibition of an oncogene, the eukaryotic translation initiation factor (eIF4E).

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33

Antolini, Floria, Peter B. Hitchcock, Alexei V. Khvostov, and Michael F. Lappert. "Synthesis and characterization of N-silylated, C1-symmetric benzamidinates of lithium, sodium, and tin(II)." Canadian Journal of Chemistry 84, no. 2 (February 1, 2006): 269–76. http://dx.doi.org/10.1139/v05-250.

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The synthesis and characterization of complexes obtained from the reactions between Li[N-t-Bu(SiMe3)] (A) or the sodium analogue Na[N-t-Bu(SiMe3)] (B) and the cyanoarene RCN (R = Ph or 4-MeOC6H4) are discussed. These are the THF adduct [Li{µ-cis-N(t-Bu)C(Ph)N(SiMe3)}(THF)]2 (1), the TMEDA adduct Li[N(t-Bu)C(Ph)N(SiMe3)](TMEDA) (2), the neutral ligand-free lithium benzamidinate Li[N(t-Bu)C(C6H4OMe-4)N(SiMe3)] (3), and the THF adduct Li[N(t-Bu)C(C6H4OMe-4)N(SiMe3)](THF) (3a). The preparation and structure of the crystalline compound [Na{µ-cis-N(t-Bu)C(Ph)N(SiMe3)}(OEt2)]2 (4) is described. From the lithium benzamidinate 1 and Sn(II) chloride the tin(II) complex [Sn{N(t-Bu)C(Ph)N(SiMe3)}2] (5) was obtained. The molecular structures of the crystalline compounds 1, 4, and 5 were established by X-ray diffraction. In 1 and 4 the benzamidinato ligand is both chelating and bridging, with the Me3Si-substituted nitrogen atom as the bridging site. The central planar (MN)2 four-membered ring is a rhombus in 1, with almost equal LiN bond lengths, whereas in 4 the bonds to Na(1) are significantly longer than those to Na(2). In 5, the ligand is N,N′-chelating. Key words: alkali metals, tin(II), benzamidinates, NMR spectra, X-ray structures.

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34

Rosenberg, Claudio L., and Mark R. Handy. "Syntectonic melt pathways during simple shearing of a partially molten rock analogue (Norcamphor-Benzamide)." Journal of Geophysical Research: Solid Earth 105, B2 (February 10, 2000): 3135–49. http://dx.doi.org/10.1029/1999jb900371.

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35

Singh, Sukhbir, Sandeep Arora, Ervon Dhalio, Neelam Sharma, Kunal Arora, and Ajmer Singh Grewal. "Design and synthesis of newer N-benzimidazol-2yl benzamide analogues as allosteric activators of human glucokinase." Medicinal Chemistry Research 30, no. 3 (January 13, 2021): 760–70. http://dx.doi.org/10.1007/s00044-020-02697-z.

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36

Swarna, Venkat Manoj, Bradley J. Undem, and Vijaya L. Korlipara. "Design and synthesis of 3,5-disubstituted benzamide analogues of DNK333 as dual NK1/NK2 receptor probes." Bioorganic & Medicinal Chemistry Letters 17, no. 4 (February 2007): 890–94. http://dx.doi.org/10.1016/j.bmcl.2006.11.064.

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37

Jayaram, Hiremagalur N., Michael Grusch, David A. Cooney, and Georg Krupitza. "Consequences of IMP Dehydrogenase Inhibition, and its Relationship to Cancer and Apoptosis." Current Medicinal Chemistry 6, no. 7 (July 1999): 561–74. http://dx.doi.org/10.2174/092986730607220401122851.

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Inosine 5'-monophosphate dehydrogenase (IMPDH) is a rate-limiting enzyme for the synthesis of GTP and dGTP. Two isoforms of IMPDH have been identified. IMPDH Type I is ubiquitous and predominantly present in normal cells, whereas IMPDH Type II is predominant in malignant cells. IMPDH plays an important role in the expression of cellular genes, such as p53, c-myc and Ki-ras. IMPDH activity is transformation and progression linked in cancer cells. IMPDH inhibitors, tiazofurin, selenazofurin, and benzamide riboside share similar mechanism of action and are metabolized to their respective NAD analogues to exert antitumor activity. Tiazofurin exhibits clinical responses in patients with acute myeloid leukemia and chronic myeloid leukemia in blast crisis. These responses relate to the level of the NAD analogue formed in the leukemic cells. Resistance to tiazofurin and related IMPDH inhibitors relate mainly to a decrease in NMN adenylyltransferase activity. IMPDH inhbitors induce apoptosis. IMPDH inhitors are valuable probes for examining biochemical functions of GTP as they selectively reduce guanylate concentration. Incomplete depletion of cellular GTP level seems to down-regulate G-protein function, thereby inhibit cell growth or induce apoptosis. Inosine 5' -monophosphate dehydrogenase (IMPDH, EC 1.1.1.205) catalyzes the dehydrogenation of IMP to XMP utilizing NAD as the proton acceptor. Studies have demonstrated that IMPDH is a rate-limiting step in the de novo synthesis of guanylates, including GTP and dGTP. The importance of IMPDH is central because dGTP is required for the DNA synthesis and GTP plays a major role not only for the cellular activity but also for cellular regulation. Two isoforms of IMPDH have been demonstrated [1]. IMPDH Type I is ubiquitous and predominately present in normal cells, whereas the IMPDH Type II enzyme is predominant in malignant cells [2]. Although guanylates could be salvaged from guanine by the enzyme hypoxanthine-guanine phosphoribosyltransferase (EC 2.4.2.8), the level of circulating guanine is low in dividing cells and this route is probably insufficient to satisfy the needs of guanylates in the cells [3].

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38

Srinivasarao, Singireddi, Adinarayana Nandikolla, Amaroju Suresh, Kevin Van Calster, Linda De Voogt, Davie Cappoen, Balaram Ghosh, Himanshu Aggarwal, Sankaranarayanan Murugesan, and Kondapalli Venkata Gowri Chandra Sekhar. "Seeking potent anti-tubercular agents: design and synthesis of substituted-N-(6-(4-(pyrazine-2-carbonyl)piperazine/homopiperazine-1-yl)pyridin-3-yl)benzamide derivatives as anti-tubercular agents." RSC Advances 10, no. 21 (2020): 12272–88. http://dx.doi.org/10.1039/d0ra01348j.

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39

Al-Hazam, Hanan A., Zeki A. Al-Shamkani, Najim A. Al-Masoudi, Bahjat A. Saeed, and Christophe Pannecouque. "New chalcones and thiopyrimidine analogues derived from mefenamic acid: microwave-assisted synthesis, anti-HIV activity and cytotoxicity as antileukemic agents." Zeitschrift für Naturforschung B 72, no. 4 (April 1, 2017): 249–56. http://dx.doi.org/10.1515/znb-2016-0223.

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AbstractThe development of new HIV non-nucleoside reverse transcriptase inhibitors offers the possibility of generating structures of increased potency. To this end, coupling of mefenamic acid (4) with 4-amino-acetophenone (6) in the presence of dicyclohexylcarbodiimide and dimethylaminopyridine (DMAP) reagents afforded 4-(acetyphenyl)-2-((2,3-dimethylphenyl)amino)benzamide (7). Analogously, treatment of mefenamyl chloride (5) prepared from 4 with 6 under microwave irradiation (MWI) afforded 7. A new series of substituted chalconyl-incorporated amide derivatives of mefenamic acid 8–13 were synthesized from condensation of 7 with various substituted benzaldehydes via the Claisen–Schmidt reaction. Treatment of 8 and 11 with thiourea in a basic medium afforded the thiopyrimidine analogues 14 and 15, respectively. The newly synthesized compounds were assayed against HIV-1 and HIV-2 in MT-4 cells. Compounds 9 and 11 showed cytotoxicity values of 2.17 and 2.06 μm, respectively, against mock-infected MT-4 cells (C type adult T leukemia cells), which considered to be promising antileukemic agents.

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Moir, Michael, Rochelle Boyd, Hendra Gunosewoyo, Andrew P. Montgomery, Mark Connor, and Michael Kassiou. "Synthesis and evaluation of various heteroaromatic benzamides as analogues of –ylidene-benzamide cannabinoid type 2 receptor agonists." Tetrahedron Letters 60, no. 36 (September 2019): 151019. http://dx.doi.org/10.1016/j.tetlet.2019.151019.

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41

Tu, Zhude, Jinbin Xu, Lynne A. Jones, Shihong Li, Craig Dumstorff, Suwanna Vangveravong, Delphine L. Chen, Kenneth T. Wheeler, Michael J. Welch, and Robert H. Mach. "Fluorine-18-Labeled Benzamide Analogues for Imaging the σ2Receptor Status of Solid Tumors with Positron Emission Tomography." Journal of Medicinal Chemistry 50, no. 14 (July 2007): 3194–204. http://dx.doi.org/10.1021/jm0614883.

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42

Diouf, O., M. Bourhim, D. M. Lambert, J. H. Poupaert, J. P. Stables, and J. Vamecq. "Anticonvulsant and neurotoxicological properties of 4-amino-N-(2-ethylphenyl)benzamide, a potent ameltolide analogue." Biomedicine & Pharmacotherapy 51, no. 3 (January 1997): 131–36. http://dx.doi.org/10.1016/s0753-3322(97)86911-9.

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43

Gradillas, Ana, Berta López, Miguel Braña, Isabel Sancho, Carmen Pérez-García, and Luis Alguacil. "Synthesis and Biological Activity of Picobenzide (3,5-Dimethyl-N-(pyridin-4-ylmethyl)benzamide) Analogues as Potential Antipsychotic Agents." Arzneimittelforschung 55, no. 12 (December 23, 2011): 725–29. http://dx.doi.org/10.1055/s-0031-1296921.

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44

Halton, Brian, Carissa S. Jones, Peter T. Northcote, and Roland Boese. "Studies in the Cycloproparene Series: Formation of a New Dimer of 1H-Cyclopropa[b]naphthalene." Australian Journal of Chemistry 52, no. 4 (1999): 285. http://dx.doi.org/10.1071/c98179.

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1-(Trimethylsilyl)-1H-cyclopropa[b]naphthalene (10) and its 1-methyl derivative (11) have been isolated as pure compounds from use of a lipophilic size exclusion gel. Acylation of the 1H-cyclopropa[b]naphthalenyl anion (2) is effected with N,N -dimethyl-benzamide and -acetamide to give (5) and (6), respectively. Analogous reactions with the 1-(trimethylsilyl)-1H-cyclopropa[b]naphthalenyl anion (9) do not yield the 1-acyl-1-(trimethylsilyl)-1H-cyclopropa[b]naphthalenes (12) and (13); instead the novel 6-methyl- 7H-dibenzo[b,g]fluorene (15) results from attempted acetylation. Compound (15), a formal dimer of 1H-cyclopropa[b]naphthalene (1), is formed also from anion (9) both in toluene and from addition of hydrocarbon (1); its structure is assigned from spectroscopic data and confirmed by single-crystal X-ray analysis.

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45

Tripathy, Swayansiddha, Mohammed Afzal Azam, Srikanth Jupudi, and Susanta Kumar Sahu. "Pharmacophore generation, atom-based 3D-QSAR, molecular docking and molecular dynamics simulation studies on benzamide analogues as FtsZ inhibitors." Journal of Biomolecular Structure and Dynamics 36, no. 12 (October 11, 2017): 3218–30. http://dx.doi.org/10.1080/07391102.2017.1384401.

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46

Bai, Suping, Shihong Li, Jinbin Xu, Xin Peng, Kiran Sai, Wenhua Chu, Zhude Tu, Chenbo Zeng, and Robert H. Mach. "Synthesis and Structure–Activity Relationship Studies of Conformationally Flexible Tetrahydroisoquinolinyl Triazole Carboxamide and Triazole Substituted Benzamide Analogues as σ2 Receptor Ligands." Journal of Medicinal Chemistry 57, no. 10 (May 12, 2014): 4239–51. http://dx.doi.org/10.1021/jm5001453.

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47

Grewal, Ajmer Singh, Rajeev Kharb, Deo Nandan Prasad, Jagdeep Singh Dua, and Viney Lather. "N-pyridin-2-yl benzamide analogues as allosteric activators of glucokinase: Design, synthesis, in vitro,in silico and in vivo evaluation." Chemical Biology & Drug Design 93, no. 3 (November 28, 2018): 364–72. http://dx.doi.org/10.1111/cbdd.13423.

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48

Sagar, Belakavadi K., Hemmige S. Yathirajan, Ravindranath S. Rathore, and Christopher Glidewell. "Four closely related N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)benzamides: order versus disorder, and similar molecular conformations but different modes of supramolecular aggregation, with a new disordered refinement of 2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophene." Acta Crystallographica Section C Structural Chemistry 74, no. 1 (January 1, 2018): 45–53. http://dx.doi.org/10.1107/s2053229617017326.

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Four closely related N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)benzamides, bearing different substituents on the benzamide ring, have been synthesized and structurally characterized. In each of N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-3-fluorobenzamide, C22H18FNO2S, (I), N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-4-chlorobenzamide, C22H18ClNO2S, (II), N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2,6-difluorobenzamide, C22H17F2NO2S, (III), and N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2-methoxybenzamide, C23H21NO3S, (IV), the last of which crystallizes with Z′ = 2 in the space group P\overline{1}, the fused six-membered ring adopts a half-chair conformation. In each of (I)–(III), this ring is disordered over two sets of atomic sites having occupancies of 0.811 (6) and 0.189 (6) in (I), 0.645 (7) and 0.355 (7) in (II), and 0.784 (6) and 0.216 (6) in (III), such that the two disorder components of the ring are almost enantiomeric. Molecules of (I) are linked into chains by π–π stacking interactions, and those of (II) are linked into chains by a C—H...π hydrogen bond. A combination of two C—H...O hydrogen bonds and two C—H...π hydrogen bonds links the molecules of (III) into complex sheets, but the molecules of (IV) are linked by a combination of two hydrogen bonds, one each of the C—H...O and C—H...π types, to form centrosymmetric tetramers. The structures of (I)–(IV) are compared with that of the unsubstituted analogue N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)benzamide and a new refinement of the parent amine 2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophene, using the original data set, has found that here too the fused six-membered ring exhibits conformational disorder, with occupancies of 0.887 (9) and 0.113 (9). Comparisons are made with some related compounds.

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49

Иванова, E. Ivanova, Мелешкин, A. Meleshkin, Скачилова, S. Skachilova, Елизарова, et al. "A Comparative Study of Toxicity and the Scale of Activity of New N-Substituted Benzamide Derivative." Journal of New Medical Technologies 22, no. 1 (February 11, 2015): 16–19. http://dx.doi.org/10.12737/9069.

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A promising search direction of modern scientists, involved in antiarrhythmic researchs, is the creation of substances that can suppress the repolarization phase of the action potential of myocardial cells. At the same time, the well-known domestic representative of this group of substances – the Nibentan – has a number of undesirable effects. To correct for these effects, the chemical compound the Nibentan with L-glutamic acid as the anion was created. In experi-ments on mice, it was found that the acute toxicity of the compound is N-substituted Benzamide derivative – Racemate Nibentan with L-glutamic acid is below 1.6 times at the intra-peritoneal injection in comparison with the acute toxicity structural analogue the Nibentan. Studied chemical compound in the range of doses from 1 to 5 % from DL50 suppresses reproduction acontinued disturbances of cardiac rhythm, which may serve as evidence of the ability of compounds to inhibit sodium ion currents through the membrane of cardiomyocytes. The compound of the Racemate Nibentan with L-glutamic acid also has a great therapeutic effect on aconitine arrhythmiac model in rats. On the model of transient ischemic arrhythmias a new compound Nibentan with comparable anti-arrhythmic activity in doses of 5 and 2.5 % from LD50, exceeds the reference product to prevent the formation of occlusion and reperfusion ventricular fibrillation in acute experience on cats. This work was supported by the project (project code - 2859) performed in Mordovia State N.P. Ogarev University under Government job and grant RFBR 14-04-31104.

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50

Campkin, David M., Yuna Shimadate, Barbara Bartholomew, Paul V. Bernhardt, Robert J. Nash, Jennette A. Sakoff, Atsushi Kato, and Michela I. Simone. "Borylated 2,3,4,5-Tetrachlorophthalimide and Their 2,3,4,5-Tetrachlorobenzamide Analogues: Synthesis, Their Glycosidase Inhibition and Anticancer Properties in View to Boron Neutron Capture Therapy." Molecules 27, no. 11 (May 26, 2022): 3447. http://dx.doi.org/10.3390/molecules27113447.

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Tetrachlorinated phthalimide analogues bearing a boron-pinacolate ester group were synthesised via two synthetic routes and evaluated in their glycosidase modulating and anticancer properties, with a view to use them in boron neutron capture therapy (BNCT), a promising radiation type for cancer, as this therapy does little damage to biological tissue. An unexpected decarbonylation/decarboxylation to five 2,3,4,5-tetrachlorobenzamides was observed and confirmed by X-ray crystallography studies, thus, giving access to a family of borylated 2,3,4,5-tetrachlorobenzamides. Biological evaluation showed the benzamide drugs to possess good to weak potencies (74.7–870 μM) in the inhibition of glycosidases, and to have good to moderate selectivity in the inhibition of a panel of 18 glycosidases. Furthermore, in the inhibition of selected glycosidases, there is a core subset of three animal glycosidases, which is always inhibited (rat intestinal maltase α-glucosidase, bovine liver β-glucosidase and β-galactosidase). This could indicate the involvement of the boron atom in the binding. These glycosidases are targeted for the management of diabetes, viral infections (via a broad-spectrum approach) and lysosomal storage disorders. Assays against cancer cell lines revealed potency in growth inhibition for three molecules, and selectivity for one of these molecules, with the growth of the normal cell line MCF10A not being affected by this compound. One of these molecules showed both potency and selectivity; thus, it is a candidate for further study in this area. This paper provides numerous novel aspects, including expedited access to borylated 2,3,4,5-tetrachlorophthalimides and to 2,3,4,5-tetrachlorobenzamides. The latter constitutes a novel family of glycosidase modulating drugs. Furthermore, a greener synthetic access to such structures is described.

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