Convenient Synthesis of Novel Quinazoline Congeners via Copper Catalyzed C-N/C-S Coupling and Their Biological Evaluation

被引：5

作者：

Lakum, Harshad P. ^{[1
]}

Shah, Dhruvin R. ^{[1
]}

Chikhalia, Kishor H. ^{[1
]}

机构：

[1] Gujarat Univ, Sch Sci, Dept Chem, Ahmadabad 380009, Gujarat, India

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2016年 / 53卷 / 01期

关键词：

1,3,4-OXADIAZOLE DERIVATIVES; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTICANCER AGENT; DESIGN; INHIBITORS; EXPLORATION; PIPERAZINE; DOCKING; SERIES;

D O I：

10.1002/jhet.2404

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A library of novel quinazoline scaffolds endowed with semicarbazide/oxadiazole thiol motif synthesized via an efficient and sustainable copper catalyzed C-N/C-S coupling is reported, making the presented methodology extremely valuable from economic and environmental point of view. Among the all synthesized compounds screened for in vitro antibacterial, antifungal, and anti-TB activity, 7b, 7c, 7f, 9b, 9c, 9i, and 9j showed excellent inhibitory effect on particular strain of bacteria, fungi, and M. tuberculosis H37Rv as well. All the newly synthesized derivatives were well characterized by their IR, H-1 NMR, C-13 NMR, mass spectroscopy as well as elemental analysis.

引用

页码：209 / 219

页数：11

共 40 条

[1] Aerobic Copper-Catalyzed Organic Reactions [J].

Allen, Scott E. ;

Walvoord, Ryan R. ;

Padilla-Salinas, Rosaura ;

Kozlowski, Marisa C. .

CHEMICAL REVIEWS, 2013, 113 (08) :6234-6458

[2] COMPARISON OF IMPROVED BACTEC AND LOWENSTEIN-JENSEN MEDIA FOR CULTURE OF MYCOBACTERIA FROM CLINICAL SPECIMENS [J].

ANARGYROS, P ;

ASTILL, DSJ ;

LIM, ISL .

JOURNAL OF CLINICAL MICROBIOLOGY, 1990, 28 (06) :1288-1291

[3] Synthesis, anti-inflammatory evaluation and docking studies of some new fluorinated fused quinazolines [J].

Balakumar, C. ;

Lamba, P. ;

Kishore, D. Pran ;

Narayana, B. Lakshmi ;

Rao, K. Venkat ;

Rajwinder, K. ;

Rao, A. Raghuram ;

Shireesha, B. ;

Narsaiah, B. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (11) :4904-4913

[4] Synthesis and biological activity of novel antibacterial quinazolines [J].

Bedi, PMS ;

Kumar, V ;

Mahajan, MP .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (20) :5211-5213

[5] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[6] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions [J].

Beletskaya, Irina P. ;

Ananikov, Valentine P. .

CHEMICAL REVIEWS, 2011, 111 (03) :1596-1636

[7] Aminoquinazolines as TRPV1 antagonists: Modulation of drug-like properties through the exploration of 2-position substitution [J].

Blum, Charles A. ;

Zheng, Xiaozhang ;

Brielmann, Harry ;

Hodgetts, Kevin J. ;

Bakthavatchalam, Rajagopal ;

Chandrasekhar, Jayaraman ;

Krause, James E. ;

Cortright, Daniel ;

Matson, David ;

Crandall, Marci ;

Ngo, Chu K. ;

Fung, Lawrence ;

Day, Marta ;

Kershaw, Mark ;

De Lombaert, Stephane ;

Chenard, Bertrand L. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (16) :4573-4577

[8] Transition-Metal-Free O-, S-, and N-Arylation of Alcohols, Thiols, Amides, Amines, and Related Heterocycles [J].

Cano, Rafael ;

Ramon, Diego J. ;

Yus, Miguel .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (02) :654-660

[9] Synthesis of novel 4,6-disubstituted quinazoline derivatives, their anti-inflammatory and anti-cancer activity (cytotoxic) against U937 leukemia cell lines [J].

Chandrika, P. Mani ;

Yakaiah, T. ;

Rao, A. Raghu Ram ;

Narsaiah, B. ;

Reddy, N. Chakra ;

Sridhar, V. ;

Rao, J. Venkateshwara .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (04) :846-852

[10] Design and synthesis of novel 7-aminoquinazoline derivatives: Antitumor and anticonvulsant activities [J].

El-Azab, Adel S. ;

ElTahir, Kamal E. H. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (05) :1879-1885

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