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新型噻唑、吡喃并噻唑、噻唑并[4,5-]吡啶和噻唑并[5',4':5,6]吡喃并[2,3-]嘧啶衍生物的合成及异吲哚啉-1,3-二酮基团的引入。

Synthesis of novel thiazole, pyranothiazole, thiazolo[4,5-]pyridines and thiazolo[5',4':5,6]pyrano[2,3-]pyrimidine derivatives and incorporating isoindoline-1,3-dione group.

作者信息

Hosny Mona A, Zaki Yasser H, Mokbel Wafaa A, Abdelhamid Abdou O

机构信息

1Department of Chemistry, Faculty of Women for Arts, Science and Education, Ain Shams University, Heliopolis, Cairo 11757 Egypt.

2Department of Chemistry, Faculty of Science, Beni-Suef University, Beni‑Suef, 62514 Egypt.

出版信息

BMC Chem. 2019 Mar 26;13(1):37. doi: 10.1186/s13065-019-0559-x. eCollection 2019 Dec.

DOI:10.1186/s13065-019-0559-x
PMID:31384785
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6661834/
Abstract

BACKGROUND

Thiazole is a core structural motif presents in a wide range of natural products. Thiazole derivatives also have a wide range of medicinal and biological properties.

RESULTS

The reaction of hydrazonoyl halides with 2-(1-(4-(1,3-dioxoisoindolin-2-yl)phenyl)ethylidene)hydrazinecarbothioamidein ethanol and triethylamine yielded 2-(4-(1-(2-(4-(2-Arylhydrazono)-5-s-4,5-dihydrothiazol-2-yl)hydrazono)-ethyl)phenyl)isoindoline-1,3-dione and 2-(4-(1-(2-(5-(2-Arylhydrazono)-4-oxo-4,5-dihydrothiazol-2-yl)hydrazono)ethyl)-phenyl)isoindoline-1,3-dione.The reaction of 2-(4-(1-(2-(4-oxo-4,5-dihydrothiazol-2-yl)hydrazono)ethyl)phenyl)isoindoline-1,3-dione with arylidenemalononitrile also yielded 5-amino-2-(2-(1-(4-(1,3-dioxoisoindolin-2-yl)phenyl)ethylidene)hydrazinyl)-7-substituted-7-pyrano[2,3-]thiazole-6-carbonitrile. The structures of the newly synthesized compound were elucidated whenever possible on the basis of elemental analysis, spectral data, and alternative synthetic routes. Three of them were evaluated against a breast cancer cell line for their antitumor activity.

CONCLUSIONS

Compound has been shown to be useful in the synthesis of a new series of 1,3-thiazole, pyrano[2,3-]thiazole and 4,5-dihydrothiazolo[4,5-]pyridine derivatives using hydrazonoyl halides as precursors. The anticancer efficacy of compounds , , and against MCF-7, a breast cancer cell line, was also compared to the standard anticancer drug doxorubicin.

摘要

背景

噻唑是多种天然产物中的核心结构单元。噻唑衍生物也具有广泛的药用和生物学特性。

结果

酰肼基卤与2-(1-(4-(1,3-二氧代异吲哚啉-2-基)苯基)亚乙基)肼基甲硫酰胺在乙醇和三乙胺中反应，生成2-(4-(1-(2-(4-(2-芳基肼基)-5-硫代-4,5-二氢噻唑-2-基)肼基)乙基)苯基)异吲哚啉-1,3-二酮和2-(4-(1-(2-(5-(2-芳基肼基)-4-氧代-4,5-二氢噻唑-2-基)肼基)乙基)苯基)异吲哚啉-1,3-二酮。2-(4-(1-(2-(4-氧代-4,5-二氢噻唑-2-基)肼基)乙基)苯基)异吲哚啉-1,3-二酮与亚苄基丙二腈反应也生成5-氨基-2-(2-(1-(4-(1,3-二氧代异吲哚啉-2-基)苯基)亚乙基)肼基)-7-取代-7-吡喃并[2,3-]噻唑-6-腈。新合成化合物的结构在可能的情况下根据元素分析、光谱数据和替代合成路线进行了阐明。其中三种化合物针对乳腺癌细胞系评估了它们的抗肿瘤活性。

结论

已证明化合物可用于以酰肼基卤为前体合成一系列新的1,3-噻唑、吡喃并[2,3-]噻唑和4,5-二氢噻唑并[4,5-]吡啶衍生物。还将化合物、和对乳腺癌细胞系MCF-7的抗癌疗效与标准抗癌药物阿霉素进行了比较。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb85/6661834/09f944a78556/13065_2019_559_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb85/6661834/716c90309303/13065_2019_559_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb85/6661834/e3ae9c0626e9/13065_2019_559_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb85/6661834/3de426dcf0e2/13065_2019_559_Sch3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb85/6661834/5d8e73784b47/13065_2019_559_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb85/6661834/09f944a78556/13065_2019_559_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb85/6661834/716c90309303/13065_2019_559_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb85/6661834/e3ae9c0626e9/13065_2019_559_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb85/6661834/3de426dcf0e2/13065_2019_559_Sch3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb85/6661834/5d8e73784b47/13065_2019_559_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb85/6661834/09f944a78556/13065_2019_559_Fig2_HTML.jpg

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