Synthesis and Antibacterial Evaluation of Novel Heterocyclic Compounds Containing a Sulfonamido Moiety

被引:77
作者
Azab, Mohammad Emad [1 ]
Youssef, Mohamed M. [2 ]
El-Bordany, Eman A. [1 ]
机构
[1] Ain Shams Univ, Fac Sci, Dept Chem, Organ Synthet Lab, Cairo 11566, Egypt
[2] Taif Univ, Fac Sci, Dept Chem, At Taif 21974, Saudi Arabia
关键词
cyanoacetylhydrazide; sulfonamide; pyridazines; pyrazoles; oxazole; pyrimidines; antibacterial activity; MICROWAVE-ASSISTED SYNTHESIS; ANALGESIC ACTIVITY; DERIVATIVES; INHIBITORS; SULFAMIDE; UTILITY; PYRIMIDINE; THIOPHENE;
D O I
10.3390/molecules18010832
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Aiming for the synthesis of new heterocyclic compounds containing a sulfonamido moiety suitable for use as antibacterial agents, the precursor ethyl {[4-N-(4,6-dimethylpyrimidin-2-yl)sulfamoyl]phenylazo}cyanoacetate was reacted with a variety of active methylene compounds producing pyran, pyridine and pyridazine derivatives. Also, the reactivity of the precursor hydrazone towards hydrazine derivatives to give pyrazole and oxazole derivatives was studied. On the other hand, treatment of the same precursor with urea, thiourea and/or guanidine hydrochloride furnished pyrimidine and thiazine derivatives, respectively. The newly synthesized compounds were tested for antibacterial activity, whereby eight compounds were found to have high activities.
引用
收藏
页码:832 / 844
页数:13
相关论文
共 25 条
[1]   Synthesis of New Visnagen and Khellin Furochromone Pyrimidine Derivatives and Their Anti-Inflammatory and Analgesic Activity [J].
Abu-Hashem, Ameen Ali ;
Youssef, Mohamed M. .
MOLECULES, 2011, 16 (03) :1956-1972
[2]  
Ammar YA, 2004, INDIAN J CHEM B, V43, P2203
[3]   The utility of 2-(5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4-yloxy) acethydrazide in heterocyclic synthesis [J].
Azab, M. E. ;
Ibraheem, M. A. E. ;
Madkour, H. M. F. .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2006, 181 (06) :1299-1313
[4]   Utility of the enaminonitrile moiety in the synthesis of some biologically active thienopyrimidine derivatives [J].
Azab, Mohammad Emad .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (07) :1766-1782
[5]  
Carrod LP, 1972, Antibiotic and Chemotherapy, V3rd, P477
[6]   Synthesis and Antiviral Activity of 5-(4-Chlorophenyl)-1,3,4-Thiadiazole Sulfonamides [J].
Chen, Zhuo ;
Xu, Weiming ;
Liu, Keming ;
Yang, Song ;
Fan, Huitao ;
Bhadury, Pinaki S. ;
Hu, De-Yu ;
Zhang, Yuping .
MOLECULES, 2010, 15 (12) :9046-9056
[7]   FRANGOMERIC AND ANCHIMERIC PROCESSES IN PREPARATION AND REACTIONS OF ALPHA-BETA-EPOXY KETONES [J].
COFFEN, DL ;
KORZAN, DG .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (03) :390-&
[8]   Carbonic anhydrase inhibitors: Crystallographic and solution binding studies for the interaction of a boron-containing aromatic sulfamide with mammalian isoforms I-XV [J].
Di Fiore, Anna ;
Monti, Simona Maria ;
Innocenti, Alessio ;
Winum, Jean-Yves ;
De Simone, Giuseppina ;
Supuran, Claudiu T. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (12) :3601-3605
[9]   Potent and selective, sulfamide-based human β3-adrenergic receptor agonists [J].
Dow, RL ;
Paight, ES ;
Schneider, SR ;
Hadcock, JR ;
Hargrove, DM ;
Martin, KA ;
Maurer, TS ;
Nardone, NA ;
Tess, DA ;
DaSilva-Jardine, P .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (12) :3235-3240
[10]  
El-Gaby MSA, 2002, ACTA CHIM SLOV, V49, P159