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Volumn 47, Issue 13, 2004, Pages 3438-3449

Synthesis, x-ray crystal structures, stabilities, and in vitro cytotoxic activities of new heteroarylacrylonitriles

Author keywords

[No Author keywords available]

Indexed keywords

2 (1H BENZIMIDAZOL 2 YL) 3 (5 NITROTHIOPHEN 2 YL)ACRYLONITRILE; 2 (5 BENZYL 1H 1,2,4 TRIAZOL 3 YL) 3 (5 NITROPHEN 2 YL)ACRYLONITRILE; ACRYLONITRILE; ACRYLONITRILE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; CASPASE 3; CASPASE 9; CISPLATIN; ETOPOSIDE; FURAN DERIVATIVE; HYDROGEN; NITRILE; PHENYL GROUP; THIOPHENE DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 2942580724     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0311036     Document Type: Article
Times cited : (46)

References (33)
  • 1
    • 0020605869 scopus 로고
    • Synthesis and spasmolytic activity of 2-substituted-3-(omega-dialkylaminoalkoxyphenyl)acrylonitriles and related compounds
    • Naruto, S.; Mizuta, H.; Yoshida, T.; Uno, H.; Kawashima, K.; Kadokawa, T.; Nishimura, H. Synthesis and spasmolytic activity of 2-substituted-3-(omega-dialkylaminoalkoxyphenyl)acrylonitriles and related compounds. Chem. Pharm. Bull. 1983, 31, 3022-2032.
    • (1983) Chem. Pharm. Bull. , vol.31 , pp. 3022-2032
    • Naruto, S.1    Mizuta, H.2    Yoshida, T.3    Uno, H.4    Kawashima, K.5    Kadokawa, T.6    Nishimura, H.7
  • 2
    • 24544442639 scopus 로고
    • Artificial estrogens. F. Triphenylacrylonitrile and its analogs
    • Grundy, J. Artificial estrogens. F. Triphenylacrylonitrile and its analogs. Chem. Rev. 1957, 57, 357.
    • (1957) Chem. Rev. , vol.57 , pp. 357
    • Grundy, J.1
  • 3
    • 0021970911 scopus 로고
    • 3,5-Disubstituted derivatives of 1,2,4-triazole, synthesis and hypotensive activity
    • Kuzmierkiewicz, W.; Foks, H.; Baranowski, M. 3,5-Disubstituted derivatives of 1,2,4-triazole, synthesis and hypotensive activity. Sci. Pharm. 1985, 53, 133-138.
    • (1985) Sci. Pharm. , vol.53 , pp. 133-138
    • Kuzmierkiewicz, W.1    Foks, H.2    Baranowski, M.3
  • 5
    • 0016592295 scopus 로고
    • Reactions of cyanomethylbenzimidazoles. II. Reaction of cyanomethylbenzimidazoles with aldehydes, methylketones and nitroso compounds
    • (a) Sawlewicz, J.; Milczarska, B.; Manowska, W. Reactions of cyanomethylbenzimidazoles. II. Reaction of cyanomethylbenzimidazoles with aldehydes, methylketones and nitroso compounds. Pol. J. Pharmacol. Pharm. 1975, 27, 187-201.
    • (1975) Pol. J. Pharmacol. Pharm. , vol.27 , pp. 187-201
    • Sawlewicz, J.1    Milczarska, B.2    Manowska, W.3
  • 6
    • 0018236320 scopus 로고
    • Studies on quantitative relationships between the structure and in vitro tuberculostatic potency of 2-cyanomethylbenzimidazole derivatives
    • (b) Kaliszan, R.; Milczarska, B.; Lega, B.; Szefer, P.; Janowiec, M. Studies on quantitative relationships between the structure and in vitro tuberculostatic potency of 2-cyanomethylbenzimidazole derivatives. Pol. J. Pharmacol. Pharm. 1978, 30, 585-91.
    • (1978) Pol. J. Pharmacol. Pharm. , vol.30 , pp. 585-591
    • Kaliszan, R.1    Milczarska, B.2    Lega, B.3    Szefer, P.4    Janowiec, M.5
  • 7
    • 0036171084 scopus 로고    scopus 로고
    • Synthesis and antimycobacterial activity of 3-aryl-, 3-cyclohexyl-, and 3-heteroaryl-substituted-2-(1H(2H)-benzotriazol-1(2)-yl)prop-2-enenitriles, prop-2-enamides and propenoic acids. II
    • (c) Sanna, P.; Carta, A.; Gherardini, L.; Rahbar Nikookar, Esmail, M. Synthesis and antimycobacterial activity of 3-aryl-, 3-cyclohexyl-, and 3-heteroaryl-substituted-2-(1H(2H)-benzotriazol-1(2)-yl)prop-2-enenitriles, prop-2-enamides and propenoic acids. II. Farmaco 2002, 57, 79-87.
    • (2002) Farmaco , vol.57 , pp. 79-87
    • Sanna, P.1    Carta, A.2    Gherardini, L.3    Rahbar Nikookar4    Esmail, M.5
  • 8
    • 85007784646 scopus 로고
    • Relation between chemical structure and antimicrobial action of nitrofuran derivatives. IV. Antitrichomonal activity in vitro
    • Fujimoto, K.; Shimizu, M.; Takase, Y.; Nakanishi, I.; Nakamura, S. Relation between chemical structure and antimicrobial action of nitrofuran derivatives. IV. Antitrichomonal activity in vitro. Chemotherapy (Tokyo) 1967, 15, 535-541.
    • (1967) Chemotherapy (Tokyo) , vol.15 , pp. 535-541
    • Fujimoto, K.1    Shimizu, M.2    Takase, Y.3    Nakanishi, I.4    Nakamura, S.5
  • 9
    • 21344469717 scopus 로고    scopus 로고
    • Synthesis and insecticidal activity of novel acrylonitrile derivatives
    • Shiba, S. A. Synthesis and insecticidal activity of novel acrylonitrile derivatives. Phosphorus Sulfur 1996, 114, 29-37.
    • (1996) Phosphorus Sulfur , vol.114 , pp. 29-37
    • Shiba, S.A.1
  • 11
    • 0036753651 scopus 로고    scopus 로고
    • Synthesis and antitumor activity of novel 2-amino-4-(3,5,5,-trimethyl-2-pyrazolino)-1,3,5-triazine derivatives
    • Brzozowski, Z.; Saczewski, F. Synthesis and antitumor activity of novel 2-amino-4-(3,5,5,-trimethyl-2-pyrazolino)-1,3,5-triazine derivatives. Eur. J. Med. Chem. 2002, 37, 709-720.
    • (2002) Eur. J. Med. Chem. , vol.37 , pp. 709-720
    • Brzozowski, Z.1    Saczewski, F.2
  • 12
    • 0001260188 scopus 로고
    • Preparation of 1-(2-benzimidazolyl)2-substituted ethylene derivatives by the Wittig reaction
    • Porousek, J. Preparation of 1-(2-benzimidazolyl)2-substituted ethylene derivatives by the Wittig reaction. Collect. Czech. Chem. Commun. 1991, 56, 1358-1360.
    • (1991) Collect. Czech. Chem. Commun. , vol.56 , pp. 1358-1360
    • Porousek, J.1
  • 13
  • 18
    • 2942553769 scopus 로고    scopus 로고
    • note
    • The structures of rotamers 11A-D were fully optimized in the gas phase using the ab initio module (direct Hartree-Fock method, 6-31G** basis set) as implemented into the SPARTAN v 5.0 program installed on a Silicon Graphics O2 workstation.
  • 20
    • 0034440818 scopus 로고    scopus 로고
    • Proteases for cell suicide: Functions and regulation of caspases
    • Chang, H. Y.; Yang, X. Proteases for cell suicide: functions and regulation of caspases. Microbiol. Mol. Biol. Rev. 2000, 64, 821-846.
    • (2000) Microbiol. Mol. Biol. Rev. , vol.64 , pp. 821-846
    • Chang, H.Y.1    Yang, X.2
  • 22
    • 0026652493 scopus 로고
    • Relationships between the aqueous chemistry and the in vitro cytotoxic activities of mixed-amine cisplatin analogues
    • Bednarski, P. J. Relationships between the aqueous chemistry and the in vitro cytotoxic activities of mixed-amine cisplatin analogues. Biochem. Pharmacol. 1992, 43, 2609-2620.
    • (1992) Biochem. Pharmacol. , vol.43 , pp. 2609-2620
    • Bednarski, P.J.1
  • 23
    • 0029753803 scopus 로고    scopus 로고
    • Tyrphostins. 6. Dimeric benzylidenemalononitrile tyrphostins: Potent inhibitors of EGF receptor tyrosine kinase in vitro
    • Gazit, A.; Osherov, N.; Gilon, C.; Levitzki, A. Tyrphostins. 6. Dimeric benzylidenemalononitrile tyrphostins: Potent inhibitors of EGF receptor tyrosine kinase in vitro. J. Med. Chem. 1996, 39, 4905-4911.
    • (1996) J. Med. Chem. , vol.39 , pp. 4905-4911
    • Gazit, A.1    Osherov, N.2    Gilon, C.3    Levitzki, A.4
  • 24
    • 0000189906 scopus 로고
    • Relative nucleophilic reactivities of amino groups and mercaptide ions in addition reactions with α,β-unsaturated compounds
    • Friedman, M.; Cavins, J. F.; Wall, J. S. Relative nucleophilic reactivities of amino groups and mercaptide ions in addition reactions with α,β-unsaturated compounds. J. Am. Chem. Soc. 1965, 87, 3672-3682.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 3672-3682
    • Friedman, M.1    Cavins, J.F.2    Wall, J.S.3
  • 25
    • 0037102011 scopus 로고    scopus 로고
    • Acrylonitrile irreversibly inactivates glyceraldehyde-3-phosphate dehydrogenase by alkylating the catalytically active cysteine 149
    • (a) Campian, E. C.; Cai, J.; Benz, F. W. Acrylonitrile irreversibly inactivates glyceraldehyde-3-phosphate dehydrogenase by alkylating the catalytically active cysteine 149. Chem.-Biol. Interact. 2002, 140, 279-291.
    • (2002) Chem.-Biol. Interact. , vol.140 , pp. 279-291
    • Campian, E.C.1    Cai, J.2    Benz, F.W.3
  • 27
    • 0021342044 scopus 로고
    • N-Acetylcysteine as an antidote in accidental acrylonitrile poisoning
    • Buchter, A.; Peter, H.; Bolt, H. M. N-Acetylcysteine as an antidote in accidental acrylonitrile poisoning. Int. Arch. Occup. Environ. Health 1984, 53, 311-319.
    • (1984) Int. Arch. Occup. Environ. Health , vol.53 , pp. 311-319
    • Buchter, A.1    Peter, H.2    Bolt, H.M.3
  • 28
    • 26844530211 scopus 로고    scopus 로고
    • Biological markers of acute acrylonitrile intoxication in rats as a function of dose and time
    • (a) Benz, F. W.; Nerland, D. E.; Corbett, D.; Li, J. Biological markers of acute acrylonitrile intoxication in rats as a function of dose and time. Fundam. Appl. Toxicol. 1997, 36, 141-148.
    • (1997) Fundam. Appl. Toxicol. , vol.36 , pp. 141-148
    • Benz, F.W.1    Nerland, D.E.2    Corbett, D.3    Li, J.4
  • 29
    • 26844542980 scopus 로고    scopus 로고
    • Dose dependence of covalent binding of acrylonitrile to tissue protein and globin in rats
    • (b) Benz, F. W.; Nerland, D. E.; Li, J.; Corbett, D. Dose dependence of covalent binding of acrylonitrile to tissue protein and globin in rats. Fundam. Appl. Toxicol. 1997, 36, 149-156.
    • (1997) Fundam. Appl. Toxicol. , vol.36 , pp. 149-156
    • Benz, F.W.1    Nerland, D.E.2    Li, J.3    Corbett, D.4
  • 30
    • 37049058402 scopus 로고
    • Triazoles. Part VII. Syntheses of substituted 1,2,4-triazoles
    • Browne, E. J.; Polya, J. B. Triazoles. Part VII. Syntheses of substituted 1,2,4-triazoles. J. Chem. Soc. 1962, 5149-5152.
    • (1962) J. Chem. Soc. , pp. 5149-5152
    • Browne, E.J.1    Polya, J.B.2
  • 31
    • 0242513246 scopus 로고
    • The preparation and reactions of 2-benzimidazolecarboxylic acid and 2-benzimidazoleacetic acid
    • Copeland, R. A. B.; Day, A. R. The preparation and reactions of 2-benzimidazolecarboxylic acid and 2-benzimidazoleacetic acid. J. Am. Chem. Soc. 1943, 65, 1072-1075.
    • (1943) J. Am. Chem. Soc. , vol.65 , pp. 1072-1075
    • Copeland, R.A.B.1    Day, A.R.2
  • 32
    • 0031946822 scopus 로고    scopus 로고
    • Decomposition of 2-propenoyl azide derivatives. Synthesis and larvicidal activity of novel products
    • Shiba, S. A. Decomposition of 2-propenoyl azide derivatives. Synthesis and larvicidal activity of novel products. Arch. Pharm. 1998, 331, 91-96.
    • (1998) Arch. Pharm. , vol.331 , pp. 91-96
    • Shiba, S.A.1
  • 33
    • 0004567750 scopus 로고
    • Anhydrous zinc chloride catalysis in carbonyl-methylene condensations: Synthesis of arylideneacetonitriles and arylidene heterocycles
    • Rao, P. Shanthan, Venkataratnam, R. V. Anhydrous zinc chloride catalysis in carbonyl-methylene condensations: synthesis of arylideneacetonitriles and arylidene heterocycles. Indian J. Chem., Sect. B 1993, 32, 484-486.
    • (1993) Indian J. Chem., Sect. B , vol.32 , pp. 484-486
    • Rao, P.S.1    Venkataratnam, R.V.2


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