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5-（呋喃-2-基）-3-（对甲苯基）-4,5-二氢-1H-吡唑-1-碳硫酰胺在合成具有抗菌活性的杂环化合物中的应用。

Utility of 5-(furan-2-yl)-3-(-tolyl)-4,5-dihydro-1-pyrazole-1-carbothioamide in the synthesis of heterocyclic compounds with antimicrobial activity.

作者信息

Abdelhamid Abdou O, El Sayed Ibrahim E, Zaki Yasser H, Hussein Ahmed M, Mangoud Mangoud M, Hosny Mona A

机构信息

1Department of Chemistry, Faculty of Science, Cairo University, Giza, 12613 Egypt.

2Department of Chemistry, Faculty of Science, El Menoufia University, Shebin El Koom, 32511 Egypt.

出版信息

BMC Chem. 2019 Apr 1;13(1):48. doi: 10.1186/s13065-019-0566-y. eCollection 2019 Dec.

DOI:10.1186/s13065-019-0566-y
PMID:31384796
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6661803/
Abstract

BACKGROUND

Pyrazolines show different biological activities. In recent years, interest in the chemistry of hydrazonoyl halides has been renewed. 1,3,4-Thiadiazoles are one of the most common heterocyclic pharmacophores with a wide range of biological activities.

RESULTS

Ethyl 2-(5-(furan-2-yl)-3-(-tolyl)-4,5-dihydro-1-pyrazol-1-yl)-4-methyl-thiazole-5-carboxylate, 2-(5-(furan-2-yl)-3-(-tolyl)-4,5-dihydro-1-pyrazol-1-yl)thiazol-4(5)-one, and 1-(2-(5-(furan-2-yl)-3-(-tolyl)-4,5-dihydro-1-pyrazol-1-yl)-4-methylthiazol-5-yl)ethan-1-one were synthesized from the reaction of 5-(furan-2-yl)-3-(-tolyl)-4,5-dihydro-1-pyrazole-1-carbothioamide with different halogenated compounds. Thiazole, 1,3,4-thiadiazole and pyrano[2,3-]thiazole derivatives were also synthesized. The structures of the newly synthesized compounds were elucidated based on elemental analysis, spectral data, and alternative synthetic routes whenever possible. Additionally, the newly synthesized compounds were screened for antimicrobial activity against various microorganisms.

CONCLUSIONS

A new series of novel functionalized 1,3,4-thiadiazoles, 1,3-thiazoles, and pyrazoline-containing moieties were synthesized using hydrazonoyl halides as precursors and evaluated for their in vitro antibacterial, and antifungal activities. The antimicrobial results of the examined compounds revealed promising results and some derivatives have activities similar to the references used.

摘要

背景

吡唑啉具有不同的生物活性。近年来，人们对卤代肼基酰卤化学的兴趣得以恢复。1,3,4-噻二唑是最常见的具有广泛生物活性的杂环药效基团之一。

结果

由5-(呋喃-2-基)-3-(对甲苯基)-4,5-二氢-1-吡唑-1-碳硫酰胺与不同的卤代化合物反应合成了2-(5-(呋喃-2-基)-3-(对甲苯基)-4,5-二氢-1-吡唑-1-基)-4-甲基噻唑-5-羧酸乙酯、2-(5-(呋喃-2-基)-3-(对甲苯基)-4,5-二氢-1-吡唑-1-基)噻唑-4(5)-酮和1-(2-(5-(呋喃-2-基)-3-(对甲苯基)-4,5-二氢-1-吡唑-1-基)-4-甲基噻唑-5-基)乙-1-酮。还合成了噻唑、1,3,4-噻二唑和吡喃并[2,3-]噻唑衍生物。尽可能根据元素分析、光谱数据和替代合成路线对新合成化合物的结构进行了阐明。此外，对新合成的化合物进行了针对各种微生物的抗菌活性筛选。

结论

以卤代肼基酰卤为前体合成了一系列新型的功能化1,3,4-噻二唑、1,3-噻唑和含吡唑啉部分，并对其体外抗菌和抗真菌活性进行了评估。所检测化合物的抗菌结果显示出有前景的结果，一些衍生物具有与所用参考物相似的活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a22e/6661803/af6203cdf413/13065_2019_566_Sch7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a22e/6661803/c55e7da58d72/13065_2019_566_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a22e/6661803/faf66935636a/13065_2019_566_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a22e/6661803/16ec4b629e9e/13065_2019_566_Sch3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a22e/6661803/5d5ae1b14cdf/13065_2019_566_Sch4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a22e/6661803/bc3d36ca7128/13065_2019_566_Sch5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a22e/6661803/1b3030a0c127/13065_2019_566_Sch6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a22e/6661803/af6203cdf413/13065_2019_566_Sch7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a22e/6661803/c55e7da58d72/13065_2019_566_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a22e/6661803/faf66935636a/13065_2019_566_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a22e/6661803/16ec4b629e9e/13065_2019_566_Sch3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a22e/6661803/5d5ae1b14cdf/13065_2019_566_Sch4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a22e/6661803/bc3d36ca7128/13065_2019_566_Sch5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a22e/6661803/1b3030a0c127/13065_2019_566_Sch6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a22e/6661803/af6203cdf413/13065_2019_566_Sch7_HTML.jpg

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