Antimycobacterial activity of novel hydrazide-hydrazone derivatives with 2H-chromene and coumarin scaffold

被引：75

作者：

Angelova, Violina T. ^{[1
]}

Valcheva, Violeta ^{[2
]}

Vassilev, Nikolay G. ^{[3
]}

Buyukliev, Rosen ^{[1
]}

Momekov, Georgi ^{[4
]}

Dimitrov, Ivan ^{[1
]}

Saso, Luciano ^{[5
]}

Djukic, Mirjana ^{[6
]}

Shivachev, Boris ^{[7
]}

机构：

[1] Med Univ Sofia, Dept Chem, Fac Pharm, 2 Dunav St, Sofia 1000, Bulgaria

[2] Bulgarian Acad Sci, Inst Microbiol, 26 Acad G Bonchev St, BU-1113 Sofia, Bulgaria

[3] Bulgarian Acad Sci, Ctr Phytochem, Inst Organ Chem, Lab Nucl Magnet Resonance, 9 Acad G Bonchev St, BU-1113 Sofia, Bulgaria

[4] Med Univ Sofia, Lab Expt Chemotherapy, Dept Pharmacol Pharmacotherapy & Toxicol, Fac Pharm, 2 Dunav St, Sofia 1000, Bulgaria

[5] Sapienza Univ, Dept Physiol & Pharmacol Vittorio Erspamer, Ple Aldo Moro 5, I-00185 Rome, Italy

[6] Univ Belgrade, Dept Toxicol, Fac Pharm, 450 Vojvode Stepe St, Belgrade 11221, Serbia

[7] Bulgarian Acad Sci, Inst Mineral & Crystallog, 107 Acad G Bonchev St, Sofia 1113, Bulgaria

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2017年 / 27卷 / 02期

关键词：

Antitmycobacterial activity; 2H-Chromene; Coumarin; Cytotoxicity; Hydrazide-hydrazone; ANTITUBERCULAR ACTIVITY; ISONIAZID DERIVATIVES; TUBERCULOSIS; DESIGN; AGENTS; TB; MDR;

D O I：

10.1016/j.bmcl.2016.11.071

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

This study reports the synthesis of new 2H-chromene or coumarin based acylhydrazones, which were evaluated for their in vitro antimycobacterial activity against reference strain Mycobacterium tuberculosis H37Rv and compared to the first-line antituberculosis drugs, isoniazid (INH) and ethambutol (EMB). The most active compounds 7m (MIC 0.13 mu M), 7o (MIC 0.15 mu M) and 7k (MIC 0.17 mu M) demonstrated antimycobacterial activity at submicromolar concentration level and remarkably minimal associated cytotoxicity in the human embryonic kidney cell line HEK-293T. Structure-activity relationship for this class of compounds has been established. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：223 / 227

页数：5

共 50 条

[31] 2-Imino 2H-chromene and 2-(phenylimino) 2H-chromene 3-aryl carboxamide derivatives as novel cytotoxic agents: synthesis, biological assay, and molecular docking study
Edraki, Najmeh
Iraji, Aida
Firuzi, Omidreza
Fattahi, Yousef
Mahdavi, Mohammad
Foroumadi, Alireza
Khoshneviszadeh, Mehdi
Shafiee, Abbas
Miri, Ramin
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2016, 13 (12) : 2163 - 2171
[32] A Forward Chemical Screen Using Zebrafish Embryos with Novel 2-Substituted 2H-Chromene Derivatives
Torregroza, Ingrid
Evans, Todd
Das, Bhaskar C.
CHEMICAL BIOLOGY & DRUG DESIGN, 2009, 73 (03) : 339 - 345
[33] COMPARISON OF RADIOPROTECTIVE ACTIVITIES OF SIMILAR SUBSTITUTED DERIVATIVES OF BENZOFURANE AND 2H-CHROMENE
FATOME, M
ANDRIEU, L
LAVAL, JD
CLAVEL, JM
BLANCO, L
GUILLAUMEL, J
RENE, L
ROYER, R
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1977, 12 (04) : 383 - 384
[34] Reaction of pregnenolone with cyanoacetylhydrazine: Novel synthesis of hydrazide-hydrazone, pyrazole, pyridine, thiazole, thiophene derivatives and their cytotoxicity evaluations
Mohareb, Rafat M.
Al-Omran, Fatima
STEROIDS, 2012, 77 (14) : 1551 - 1559
[35] Apoptosis induction of 2H-chromene derivatives on human breast cancer cells
Ardestani, S. K.
Pordeli, M.
Safavi, M.
FEBS JOURNAL, 2015, 282 : 256 - 256
[36] On the Photodegradation of Some 2H-Chromene Derivatives in Fluid Solution or in Polyurethane Matrix
Alberti, Angelo
Campredon, Mylene
Demadrille, Renaud
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2011, 84 (05) : 552 - 561
[37] Synthesis, cytotoxicity against cancer and normal cell lines of novel hydrazide-hydrazone derivatives bearing 5H-chromen-5-one
Mohareb, Rafat M.
EL-Sharkawy, Karam A.
Al Farouk, Fatma Omar
MEDICINAL CHEMISTRY RESEARCH, 2019, 28 (11) : 1885 - 1900
[38] A convenient general synthesis of 3-substituted 2H-chromene derivatives
Kaye, PT
Nocanda, XW
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (10): : 1318 - 1323
[39] Efficient synthesis of 2H-chromene derivatives via a dual-organocatalytic reaction
Somprasong, Siriphong
Prasitwatcharakorn, Watcharapon
Luanphaisarnnont, Torsak
TETRAHEDRON LETTERS, 2020, 61 (42)
[40] Electrochemical Oxidative Annulation of Inactivated Alkynes for the Synthesis of Sulfonated 2H-Chromene Derivatives
Thondur, Jagadeesh Reddy
Sharada, Duddu S.
Satyanarayana, Gedu
ORGANIC LETTERS, 2023, 25 (16) : 2793 - 2797

← 1 2 3 4 5 →