Moustafa Mohamed A, Gineinah Magdy M, Nasr Magda N, Bayoumi Waleed A H
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, King Abdulazis University, Geddah, Saudi Arabia.
Arch Pharm (Weinheim). 2004 Aug;337(8):427-33. doi: 10.1002/ardp.200300847.
New sydnone derivatives bearing a substituted phenyl ring at the 3-position have been synthesized. Two separate series of 3-(carboxyphenyl)sydnone derivatives have been prepared by cyclization of the corresponding N-nitroso-N-(carboxyphenyl)-glycine 3. The obtained 3-(carboxyphenyl)sydnones 4 were subjected to a series of different chemical reactions on the carboxylic acid group. Compound 5, the potassium salt of 4a, was reacted with alpha-chloroacetanilide derivatives 6 to give the corresponding esters 7. On the other hand, the acid hydrazide 9 was condensed with different aromatic aldehydes to give the corresponding arylidene derivatives 10. The synthesized compounds were tested for their antibacterial activities against both gram-positive and gram-negative organisms. Some of the test compounds exhibited high activity; among them, 10d is considered to be a lead compound possessing high broad-spectrum antibacterial activity.
已合成了在3-位带有取代苯环的新型 sydnone 衍生物。通过相应的N-亚硝基-N-(羧基苯基)-甘氨酸3的环化反应制备了两个独立系列的3-(羧基苯基)sydnone衍生物。所得到的3-(羧基苯基)sydnones 4在羧酸基团上进行了一系列不同的化学反应。化合物5，即4a的钾盐，与α-氯乙酰苯胺衍生物6反应得到相应的酯7。另一方面，酸肼9与不同的芳香醛缩合得到相应的亚芳基衍生物10。对合成的化合物针对革兰氏阳性和革兰氏阴性生物体的抗菌活性进行了测试。一些测试化合物表现出高活性；其中，10d被认为是具有高广谱抗菌活性的先导化合物。
