Hozien Z A, Abdel-Wahab A A, Hassan K M, Atta F M, Ahmed S A
Chemistry Department, Faculty of Science, Assiut University, Egypt.
Pharmazie. 1997 Oct;52(10):753-8.
The key compound 1-amino-8-iminocyclopenta[b]thieno[2,3-d]pyrimidine (5g) was prepared by reaction of 2-amino-3-cyano cyclopenta[b]thiophene (1) with triethyl orthoformate followed by cyclization with hydrazine hydrate in ethanol. Refluxing of 1 with triethyl orthoformate in the presence of acetic anhydride gave an unexpected product 2. while reaction with aromatic amines gave the condensation products 4a-c. Reaction of 5g with formic acid, other formate derivatives, ethoxymethylenemalononitrile and ethyl ethoxymethylenecyanoacetate gave the same product cyclopentathieno-[2,3-d]-1,2,4-triazolo[3,2-f]pyrimidine 6. Compound 7 was prepared by different methods. Treatment of 5g with dicarbonyl compounds gave the triazol derivatives 8-11. Reaction of 5g with phenyl isothiocyanate, carbon disulphide and ethyl chloroformate gave the corresponding derivatives 12-14, respectively. Condensation of 5g with some selected aromatic and heterocyclic aldehydes, acetone, N-acetyl isatin and isatin gave the condensation products 15a-e, 16-18, respectively in good yields. Many of the synthesized compounds were tested in vitro for their inhibitory activity against a variety of bacteria such as: Serratia rhodnii, Bacillus cereus, Staphylococcus citreus and Pseudomonas aeruginosa and fungi such as: Aspergillus flavus, Penicillium chrysogenum and Alternaria alternarta. Some compounds showed modest activity.
关键化合物1-氨基-8-亚氨基环戊并[b]噻吩并[2,3-d]嘧啶（5g）是通过2-氨基-3-氰基环戊并[b]噻吩（1）与原甲酸三乙酯反应，然后在乙醇中与水合肼环化制备的。1与原甲酸三乙酯在乙酸酐存在下回流得到意外产物2。而与芳香胺反应得到缩合产物4a - c。5g与甲酸、其他甲酸衍生物、乙氧基甲叉丙二腈和乙氧基甲叉氰乙酸乙酯反应得到相同产物环戊噻吩并[2,3-d]-1,2,4-三唑并[3,2-f]嘧啶6。化合物7通过不同方法制备。5g与二羰基化合物反应得到三唑衍生物8 - 11。5g与苯基异硫氰酸酯、二硫化碳和氯甲酸乙酯反应分别得到相应衍生物12 - 14。5g与一些选定的芳香醛和杂环醛、丙酮、N-乙酰异吲哚酮和异吲哚酮缩合分别以良好产率得到缩合产物15a - e、16 - 18。许多合成化合物在体外测试了它们对多种细菌如：罗得西亚沙雷氏菌、蜡样芽孢杆菌、柠檬色葡萄球菌和铜绿假单胞菌以及真菌如：黄曲霉、产黄青霉和链格孢的抑制活性。一些化合物表现出适度的活性。
