A combinatorial access to 1,5-benzodiazepine derivatives and their evaluation for aldose reductase inhibition

被引：17

作者：

Pozarentzi, Minodora ^{[1
]}

Stephanidou-Stephanatou, Julia ^{[1
]}

Tsoleridis, Constantinos A. ^{[1
]}

Zika, Chariklia ^{[2
]}

Demopoulos, Vassilis ^{[2
]}

机构：

[1] Aristotle Univ Thessaloniki, Dept Chem, Organ Chem Lab, Thessaloniki 54124, Macedonia, Greece

[2] Aristotle Univ Thessaloniki, Sch Pharm, Dept Pharmaceut Chem, Thessaloniki 54124, Macedonia, Greece

来源：

TETRAHEDRON | 2009年 / 65卷 / 36期

关键词：

Aldose reductase inhibitors; Aryldiazepinothiophenones; Benzodiazepines; o-Phenylenediamines; Mercaptopropionic acid; Multicomponent reaction; Thiazolo[3,4-a][1,3]benzimidazoles; ONE-POT SYNTHESIS; SOLVENT-FREE CONDITIONS; CYCLOADDITION; ACID; 1H,3H-THIAZOLO<3,4-A>BENZIMIDAZOLES; 1,5-BENZOTHIAZEPINES; BENZOHETEROAZEPINE; RECEPTOR; AGENTS; CNS;

D O I：

10.1016/j.tet.2009.06.080

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aryldiazepinothiophenones 4 were prepared from the reaction of o-phenylenediamines with acetone in the presence of 2-mercaptocarboxylic acids along with thiazolobenzodiazepines 6, thiazolobenzimidazoles 7 and 1,5-benzodiazepines 5, which were obtained as by-products. The benzodiazepinothiophenones 4a-d and the benzodiazepines 5a-d were also isolated from the reaction of o-phenylenediamines 1a-c with phorone. Structural assignments of the new compounds as well as complete assignment of H-1 and C-13 NMR signals were based on the analysis of their H-1 and C-13 NMR (1 D and 2D), IR, MS and elemental analysis data. Compounds 4 were evaluated for aldose reductase inhibition and also as antioxidants. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：7741 / 7751

页数：11

共 50 条

[31] Circular Dichroism Studies on New Optically Active 1,5-Benzodiazepine Derivatives
Khan, K. M.
Malik, F.
Hasan, M.
Perveen, S.
Zeitschrift fuer Naturforschung. B, Journal of Chemical Sciences, 51 (04):
[32] Assessment of elementary derivatives of 1,5-benzodiazepine as anticancer agents with synergy potential
Gawandi, Sinthiya J.
Desai, Vidya G.
Joshi, Shrinivas
Shingade, Sunil
Pissurlenkar, Raghuvir R.
BIOORGANIC CHEMISTRY, 2021, 117
[33] NbCl5 as an Efficient Catalyst for the Synthesis of 1,5-Benzodiazepine Derivatives
Gao, Shu-Tao
Liu, Wei-Hua
Ma, Jing-Jun
Wang, Chun
Liang, Qian
SYNTHETIC COMMUNICATIONS, 2009, 39 (18) : 3278 - 3284
[34] An expeditious synthesis of 1,5-benzodiazepine derivatives catalysed by zinc acetate dihydrate
Pasha, M. A.
Jayashankara, V. P.
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 15 (04) : 397 - 398
[35] Circular dichroism studies on new optically active 1,5-benzodiazepine derivatives
Khan, KM
Malik, F
Hasan, M
Perveen, S
Frelek, J
Snatzke, G
Voelter, W
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1996, 51 (04): : 588 - 598
[36] Novel isoxazole linked 1,5-benzodiazepine derivatives: Design, synthesis, molecular docking and antimicrobial evaluation
Al-Ghulikah, Hanan
Ibrahim, Sana
Ghabi, Ameni
Mtiraoui, Hasan
Jeanneau, Erwann
Msaddek, Moncef
JOURNAL OF MOLECULAR STRUCTURE, 2023, 1272
[37] Synthesis of 1H-1,5-Benzodiazepine derivatives and pyridinylquinoxalines with heterocyclic ketones
Jung, Dai-il
Song, Ju-hyun
Kim, Yong-hwan
Lee, Do-hun
Lee, Yong-gyun
Park, Yu-mi
Choi, Soon-kyu
Hahnt, Jung-tai
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2007, 28 (10) : 1877 - 1880
[38] Circular dichroism studies on new optically active 1,5-benzodiazepine derivatives
Abt. fur Physikalische Biochemie, Physiologisch-chemisches Institut, Universität Tübingen, Hoppe-Seyler-Straße 4, D-72076 Tübingen, Germany
不详
不详
Z. Naturforsch. Sect. B J. Chem. Sci., 4 (588-598):
[39] p-nitrobenzoic acid promoted synthesis of 1,5-benzodiazepine derivatives
Varala, Ravi
Enugala, Ramu
Adapa, Srinivas R.
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2007, 18 (02) : 291 - 296
[40] BIOTRANSFORMATION OF A 1,5-BENZODIAZEPINE, TRIFLUBAZAM, BY MAN
ALTON, KB
GRIMES, RM
SHAW, C
PATRICK, JE
MCGUIRE, JL
DRUG METABOLISM AND DISPOSITION, 1975, 3 (05) : 352 - 360

← 1 2 3 4 5 →