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一些1-[(N,N-二取代硫代氨基甲酰硫基)乙酰基]-3-(2-噻吩基)-5-芳基-2-吡唑啉衍生物的合成及其抗菌和抗真菌活性研究。

Synthesis of some 1-[(N, N-disubstituted thiocar bamoylthio)acetyl]-3-(2-thienyl)-5-aryl-2-pyrazoline derivatives and investigation of their antibacterial and antifungal activities.

作者信息

Turan-Zitouni Gulhan, Ozdemir Ahmet, Güven Kiymet

机构信息

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, 26470, Eskişehir, Turkey.

出版信息

Arch Pharm (Weinheim). 2005 Mar;338(2-3):96-104. doi: 10.1002/ardp.200400935.

Abstract

Fourteen new 1-[(N, N-disubstituted thiocarbamoylthio)acetyl]-3-(2-thienyl)-5-aryl-2-pyrazoline derivatives (7a-n) were synthesised by reacting 1-(chloroacetyl)-3-(2-thienyl)-5-aryl-2-pyrazolines (5a-g) and appropriate sodium salts of N, N-disubstituted dithiocarbamoic acids (6a, b). The structures of the synthesised compounds were confirmed by elemental analyses, UV, IR, (1)H-NMR and FAB(+)-MS spectral data. Their antibacterial activities against Proteus vulgaris (NRRL B-123), Escherichia coli (NRRL B-3704), Aeromonas hydrophila (Ankara University, Faculty of Veterinary Sciences), Salmonella typhimurium (NRRL B-4420), Streptococcus feacalis (NRRL B-14617), Micrococcus luteus (NRLL B-4375) were investigated and in this investigation, a significant level of activity was illustrated. Antifungal activities of the compounds against Candida albicans and Candida globrata (isolates obtained from Osmangazi Uni. Fac. of Medicine) were found to be inactive. Compounds 7c-n were also evaluated for antituberculosis activity against Mycobacterium tuberculosis H(37)Rv using the BACTEC 460 radiometric system and BACTEC 12B medium. The preliminary results indicated that all of the tested compounds were inactive against the test organism.

摘要

通过使1-(氯乙酰基)-3-(2-噻吩基)-5-芳基-2-吡唑啉(5a - g)与N,N-二取代二硫代氨基甲酸盐(6a,b)的适当钠盐反应,合成了14种新的1-[(N,N-二取代硫代氨基甲酰硫基)乙酰基]-3-(2-噻吩基)-5-芳基-2-吡唑啉衍生物(7a - n)。通过元素分析、紫外光谱、红外光谱、(1)H - NMR和FAB(+) - MS光谱数据确认了合成化合物的结构。研究了它们对普通变形杆菌(NRRL B - 123)、大肠杆菌(NRRL B - 3704)、嗜水气单胞菌(安卡拉大学兽医学院)、鼠伤寒沙门氏菌(NRRL B - 4420)、粪肠球菌(NRRL B - 14617)、藤黄微球菌(NRLL B - 4375)的抗菌活性,在该研究中,显示出显著的活性水平。发现这些化合物对白色念珠菌和光滑念珠菌(从奥斯曼加齐大学医学院分离得到)的抗真菌活性无活性。还使用BACTEC 460放射性系统和BACTEC 12B培养基评估了化合物7c - n对结核分枝杆菌H(37)Rv的抗结核活性。初步结果表明,所有测试化合物对测试生物体均无活性。

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