Green synthesis of novel quinoxaline sulfonamides with antibacterial activity

被引：25

作者：

Alavi, Sima ^{[1
,2
]}

Mosslemin, Mohammad Hossein ^{[2
]}

Mohebat, Razieh ^{[2
]}

Massah, Ahmad Reza ^{[1
]}

机构：

[1] Islamic Azad Univ, Shahreza Branch, Dept Chem, Shahreza 31186145, Isfahan, Iran

[2] Islamic Azad Univ, Yazd Branch, Dept Chem, Yazd 89195155, Iran

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 2017年 / 43卷 / 08期

关键词：

Quinoxaline; Catalyst-free; Sulfonamide; Solvent-free; Antibacterial activity; ANTIFUNGAL ACTIVITY; ACID CATALYST; DERIVATIVES; EFFICIENT; INHIBITORS; AGENTS; ANTICANCER;

D O I：

10.1007/s11164-017-2895-6

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A facile and efficient method was investigated for the synthesis of different quinoxalines by the reaction of o-phenylene diamine and 2-bromoacetophenones. This procedure was carried out in ethanol under catalyst-free conditions. Several sulfonamides were synthesized from 2-(4-methoxyphenyl)-quinoxaline in two steps. At first chlorosulfonation of 2-(4-methoxyphenyl) quinoxaline was done using chlorosulfonic acid and led to 2-methoxy-5-quinoxalin-2-yl-benzenesulfonyl chloride. Then quinoxaline sulfonamides were synthesized by the reaction of quinoxaline sulfonyl chloride with different aromatic amines under solvent-free conditions. All the products were obtained in excellent yields after an easy work-up and were evaluated for antibacterial activities against Staphylococcus spp. and Escherichia coli bacteria.

引用

页码：4549 / 4559

页数：11

共 33 条

[1] Direct and catalytic synthesis of quinoxaline derivatives from epoxides and ene-1,2-diamines
Antoniotti, S
Duñach, E
[J]. TETRAHEDRON LETTERS, 2002, 43 (22) : 3971 - 3973
[2] Ugi-Based Approaches to Quinoxaline Libraries
Azuaje, Jhonny
El Maatougui, Abdelaziz
Garcia-Mera, Xerardo
Sotelo, Eddy
[J]. ACS COMBINATORIAL SCIENCE, 2014, 16 (08) : 403 - 411
[3] Badran M. M., 2005, MED CHEM, V48, P2019
[4] Design, synthesis and biological activities of novel 5-isopropyl-2-methylphenolhydrazide-based sulfonamide derivatives
Bagul, Suresh D.
Rajput, Jamatsing D.
Tadavi, Samina K.
Bendre, Ratnamala S.
[J]. RESEARCH ON CHEMICAL INTERMEDIATES, 2017, 43 (04) : 2241 - 2252
[5] Development of potential antitumor agents. Synthesis and biological evaluation of a new set of sulfonamide derivatives as histone deacetylase inhibitors
Bouchain, G
Leit, S
Frechette, S
Abou Khalil, E
Lavoie, R
Moradei, O
Woo, SH
Fournel, M
Yan, PT
Kalita, A
Trachy-Bourget, MC
Beaulieu, C
Li, ZM
Robert, MF
MacLeod, AR
Besterman, JM
Delorme, D
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (05) : 820 - 830
[6] Brown D. J., 2004, CHEM HETEROCYCLIC CO, V61
[7] Camargo-Ordoñez A, 2011, QUIM NOVA, V34, P787, DOI 10.1590/S0100-40422011000500011
[8] Synthesis of Aryl Sulfonamides via Palladium-Catalyzed Chlorosulfonylation of Arylboronic Acids
DeBergh, J. Robb
Niljianskul, Nootaree
Buchwald, Stephen L.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (29) : 10638 - 10641
[9] Fahimi N, 2016, IRAN J CATAL, V6, P161
[10] DNA sequence specificity for topoisomerase II poisoning by the quinoxaline anticancer drugs XK469 and CQS
Gao, HL
Yamasaki, EF
Chan, KK
Shen, LL
Snapka, RM
[J]. MOLECULAR PHARMACOLOGY, 2003, 63 (06) : 1382 - 1388

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