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Synthesis and Antimicrobial Activity of Novel Piperidinyl Tetrahydrothieno[2,3-c]isoquinolines and Related Heterocycles.
ACS Omega ( IF 3.7 ) Pub Date : 2019-12-30 , DOI: 10.1021/acsomega.9b02604 Remon M Zaki 1 , Adel M Kamal El-Dean 1 , Shaban M Radwan 1 , Asmaa S A Sayed 1
ACS Omega ( IF 3.7 ) Pub Date : 2019-12-30 , DOI: 10.1021/acsomega.9b02604 Remon M Zaki 1 , Adel M Kamal El-Dean 1 , Shaban M Radwan 1 , Asmaa S A Sayed 1
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A novel series of 1-amino-2-substituted-5-piperidinyl-6,7,8,9-tertahydrothieno[2,3-c]isoquinolines (4a-e) was synthesized upon treatment of 4-cyano-1-piperidinyl-5,6,7,8-tetrahydroisoquinline-3(2H)-thione (2) with α-halo carbonyl compounds such as chloroacetone, ethyl chloroacetate, 2-bromoacetophenone, chloroacetamide, and chloroacetanilide. Construction the pyrrolyl ring associated with the thienotetrahydroisoquinoline moiety was achieved by treatment of compounds 4a, b with 2,5-dimethoxytertahydrofuran in acetic acid. 1-Pyrrolyl-2-substituted-thieno[2,3-c]isoquinolines 5a and 5b which in turn were used as multipurpose precursors for synthesis of other new heterocycles. Assignments of the chemical structures of the respectively synthesized thienotetrahydroisoquinolines and their derivatives were established on the bases of elemental and spectral techniques (Fourier transform infrared, 1H NMR, 13C NMR, and mass spectroscopy). Furthermore, certain compounds were screened for their antimicrobial activity which revealed promising activities against various pathogenic strains of bacteria and fungi.
中文翻译：
新型哌啶基四氢噻吩并[2,3-c]异喹啉及相关杂环的合成和抗菌活性。
通过处理 4-氰基-1-哌啶基，合成了一系列新型 1-氨基-2-取代-5-哌啶基-6,7,8,9-四氢噻吩并[2,3-c]异喹啉 (4a-e) -5,6,7,8-四氢异喹啉-3(2H)-硫酮(2)与α-卤代羰基化合物如氯丙酮、氯乙酸乙酯、2-溴苯乙酮、氯乙酰胺和氯乙酰苯胺。通过在乙酸中用2,5-二甲氧基四氢呋喃处理化合物4a、b来构建与噻吩并四氢异喹啉部分缔合的吡咯环。 1-吡咯基-2-取代的噻吩并[2,3-c]异喹啉5a和5b又被用作合成其他新杂环的多用途前体。基于元素和光谱技术（傅里叶变换红外、1H NMR、13C NMR和质谱）确定了分别合成的噻吩并四氢异喹啉及其衍生物的化学结构。此外，还对某些化合物的抗菌活性进行了筛选，结果显示其对各种细菌和真菌的致病菌株具有良好的活性。
更新日期：2020-01-14
中文翻译：
新型哌啶基四氢噻吩并[2,3-c]异喹啉及相关杂环的合成和抗菌活性。
通过处理 4-氰基-1-哌啶基，合成了一系列新型 1-氨基-2-取代-5-哌啶基-6,7,8,9-四氢噻吩并[2,3-c]异喹啉 (4a-e) -5,6,7,8-四氢异喹啉-3(2H)-硫酮(2)与α-卤代羰基化合物如氯丙酮、氯乙酸乙酯、2-溴苯乙酮、氯乙酰胺和氯乙酰苯胺。通过在乙酸中用2,5-二甲氧基四氢呋喃处理化合物4a、b来构建与噻吩并四氢异喹啉部分缔合的吡咯环。 1-吡咯基-2-取代的噻吩并[2,3-c]异喹啉5a和5b又被用作合成其他新杂环的多用途前体。基于元素和光谱技术（傅里叶变换红外、1H NMR、13C NMR和质谱）确定了分别合成的噻吩并四氢异喹啉及其衍生物的化学结构。此外，还对某些化合物的抗菌活性进行了筛选，结果显示其对各种细菌和真菌的致病菌株具有良好的活性。
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