Synthesis and Properties of 4-(2,5-Dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzenesulfonamide

被引：0

作者：

Kolyamshin, O. A. ^{[1
]}

Mitrasov, Yu. N. ^{[2
]}

Avruyskaya, A. A. ^{[2
]}

Danilov, V. A. ^{[1
]}

Pyl'chikova, Yu. Yu. ^{[1
]}

机构：

[1] Ulyanov Chuvash State Univ, Cheboksary 428015, Russia

[2] Yakovlev Chuvash State Pedag Univ, Cheboksary 428000, Russia

来源：

RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2023年 / 93卷 / SUPPL 2期

关键词：

4-aminobenzenesulfonamide; maleic anhydride; maleimides; succinimides; mass spectrometry; IR and H-1 NMR spectroscopy; DESIGN; INHIBITORS;

D O I：

10.1134/S1070363223150082

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of 4-aminobenzenesulfonamide with maleic anhydride gave (Z)-4-N-[4-(aminosulfonyl)phenyl)]amino-4-oxo-but-2-enoic acid, which was reacted with p-toluenesulfonic acid to obtain 4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzenesulfonamide. The latter enters the aza-Michael reaction with secondary amines to form 4-[3-(N,N-dialkylamino)]-2,5-dioxo-2,3,4,5-tetrahydro-1H-pyrrole-1-yl)benzenesulfonamides.

引用

页码：S472 / S477

页数：6

共 26 条

[1] Synthesis, characterization, biological activities and molecular modeling of Schiff bases of benzene sulfonamides bearing curcumin scaffold [J].

Ahmed, Mahmood ;

Qadir, Muhammad Abdul ;

Shafiq, Muhammad Imtiaz ;

Muddassar, Muhammad ;

Samra, Zahoor Qadir ;

Hameed, Abdul .

ARABIAN JOURNAL OF CHEMISTRY, 2019, 12 (01) :41-53

[2] Sulfonamides containing curcumin scaffold: Synthesis, characterization, carbonic anhydrase inhibition and molecular docking studies [J].

Ahmed, Mahmood ;

Qadir, Muhammad Abdul ;

Hameed, Abdul ;

Arshad, Muhammad Nadeem ;

Asiri, Abdullah M. ;

Muddassar, Muhammad .

BIOORGANIC CHEMISTRY, 2018, 76 :218-227

[3] Molecular design, synthesis and biological evaluation of cyclic imides bearing benzenesulfonamide fragment as potential COX-2 inhibitors. Part 2 [J].

Al-Suwaidan, Ibrahim A. ;

Alanazi, Amer M. ;

El-Azab, Adel S. ;

Al-Obaid, Abdulrahman M. ;

ElTahir, Kamal E. H. ;

Maarouf, Azza R. ;

Abu El-Enin, Mohamed A. ;

Abdel-Aziz, Alaa A-M .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (09) :2601-2605

[4]

[Anonymous], 1978, SW Patent, Patent No. 598214

[5]

[Anonymous], 1968, [No title captured], Patent No. 21433

[6]

[Anonymous], 1968, [No title captured], Patent No. 30308

[7]

[Anonymous], 1976, SW Patent, Patent No. 583226

[8] Discovery and structure-activity relationships of phenyl benzenesulfonylhydrazides as novel indoleamine 2,3-dioxygenase inhibitors [J].

Cheng, Ming-Fu ;

Hung, Ming-Shiu ;

Song, Jen-Shin ;

Lin, Shu-Yu ;

Liao, Fang-Yu ;

Wu, Mine-Hsine ;

Hsiao, Wenchi ;

Hsieh, Chia-Ling ;

Wu, Jian-Sung ;

Chao, Yu-Sheng ;

Shih, Chuan ;

Wu, Su-Ying ;

Ueng, Shau-Hua .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (15) :3403-3406

[9] Design, cytotoxic effects on breast cancer cell line (MDA-MB 231), and molecular docking of some maleimide-benzenesulfonamide derivatives [J].

Dhumad, Adil M. ;

Jassem, Ahmed M. ;

Alharis, Raed A. ;

Almashal, Faeza A. .

JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2021, 98 (04)

[10] Synthesis and antibacterial activity of some 5-guanylhydrazone/thiocyanato-6-arylimidazo[2,1-b]-1,3,4-thiadiazole-2-sulfonamide derivatives [J].

Gadad, AK ;

Mahajanshetti, CS ;

Nimbalkar, S ;

Raichurkar, A .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2000, 35 (09) :853-857

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