Srinivas Avula, Sunitha Malladi, Karthik Pulluri, Reddy K Vasumathi
Acta Chim Slov. 2017 Dec;64(4):1030-1041. doi: 10.17344/acsi.2017.3805.
A new series of 5-((3aR,5S,6S,6aR)-6-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-3-(4-fluorophenyl)-2,6-diphenyl-3,3a,5,6-tetrahydro-2H-pyrazolo[3,4-d]thiazoles 10a-r was synthesized by the reaction of chalcone derivatives of 2-((3aR,5S,6S,6aR)-6-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-3-phenylthiazolidin-4-one 9 with aryl/alkyl hydrazines. The chemical structures of newly synthesized compounds were elucidated by IR, NMR, MS and elemental analysis. The compounds 10a-r were evaluated for their nematicidal activity against Dietylenchus myceliophagus and Caenorhabditis elegans by aqueous in vitro screening technique. Among them, compounds containing N-benzylpyrazole moiety (10d, 10j, 10p), and N- methylpyrazole moiety (10f, 10i, 10r) showed significant nematicidal activity against both tested nematodes with LD50 160-210 ppm, almost equal to oxamyl standard. Further, these compounds 10a-r were screened for their antifungal (MZI, MIC, and MFC) activity against four fungal organisms viz, Candida albicans (ATCC 102331), Aspergillus fumigates (HIC 6094), Trichophyton rubrum (IFO 9185) and Trichophyton mentagrophytes (IFO 40996). Most of the new compounds showed appreciable activity against the tested fungi, and emerged as potential molecules for further development.
通过2-((3aR,5S,6S,6aR)-6-((1-(4-氯苯基)-1H-1,2,3-三唑-4-基)甲氧基)-2,2-二甲基四氢呋喃并[2,3-d][1,3]二氧杂环戊-5-基)-3-苯基噻唑烷-4-酮9的查尔酮衍生物与芳基/烷基肼反应，合成了一系列新的5-((3aR,5S,6S,6aR)-6-((1-(4-氯苯基)-1H-1,2,3-三唑-4-基)甲氧基)-2,2-二甲基四氢呋喃并[2,3-d][1,3]二氧杂环戊-5-基)-3-(4-氟苯基)-2,6-二苯基-3,3a,5,6-四氢-2H-吡唑并[3,4-d]噻唑10a - r。通过红外光谱、核磁共振、质谱和元素分析对新合成化合物的化学结构进行了阐明。采用水相体外筛选技术，对化合物10a - r对食菌茎线虫和秀丽隐杆线虫的杀线虫活性进行了评价。其中，含有N-苄基吡唑部分(10d、10j、10p)和N-甲基吡唑部分(10f、10i、10r)的化合物对两种受试线虫均表现出显著的杀线虫活性，半数致死剂量为160 - 210 ppm，几乎与杀线威标准品相当。此外，对这些化合物10a - r针对四种真菌生物体，即白色念珠菌(ATCC 102331)、烟曲霉(HIC 6094)、红色毛癣菌(IFO 9185)和须癣毛癣菌(IFO 40996)的抗真菌活性(最小抑菌浓度、最低抑菌浓度和最小杀菌浓度)进行了筛选。大多数新化合物对受试真菌表现出可观的活性，并成为进一步开发的潜在分子。
