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1-苄基吲哚杂合硫代氨基脲作为竞争性酪氨酸酶抑制剂的设计、合成及研究

Design, synthesis, and and study of 1-benzyl-indole hybrid thiosemicarbazones as competitive tyrosinase inhibitors.

作者信息

Batool Zahra, Ullah Saeed, Khan Ajmal, Siddique Farhan, Nadeem Sumaira, Alshammari Abdulrahman, Albekairi Norah A, Talib Rimsha, Al-Harrasi Ahmed, Shafiq Zahid

机构信息

Institute of Chemical Sciences, Bahauddin Zakariya University Multan-60800 Pakistan

Natural and Medical Sciences Research Centre, University of Nizwa P.O. Box 33, PC 616, Birkat Al Mauz Nizwa Sultanate of Oman

出版信息

RSC Adv. 2024 Sep 6;14(39):28524-28542. doi: 10.1039/d4ra05015k. eCollection 2024 Sep 4.

DOI:10.1039/d4ra05015k
PMID:39247501
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11378339/
Abstract

Developing new anti-tyrosinase drugs seems crucial for the medical and industrial fields since irregular melanin synthesis is linked to the resurgence of several skin conditions, including melanoma, and the browning of fruits and vegetables. A novel series of N-1 and C-3 substituted indole-based thiosemicarbazones 5(a-r) are synthesized and further analyzed for their inhibition potential against tyrosinase enzyme through assays. The synthesized compounds displayed very good to moderate inhibition with half maximal inhibitory concentration in the range of 12.40 ± 0.26 μM to 47.24 ± 1.27 μM. Among all the derivatives 5k displayed the highest inhibitory activity. According to SAR analysis, the derivatives with 4-substitution at the benzyl or phenyl ring of the thiosemicarbazones exhibited better inhibitory potential against tyrosinase. analysis (including ADMET prediction and molecular docking) was conducted and compared with the standard drug (kojic acid). These findings may help the hunt for new melanogenesis inhibitors that the food and cosmetics industries may find valuable.

摘要

开发新型抗酪氨酸酶药物对于医学和工业领域似乎至关重要，因为黑色素合成异常与多种皮肤疾病（包括黑色素瘤）的复发以及水果和蔬菜的褐变有关。合成了一系列新型的N-1和C-3取代的吲哚基硫代氨基脲5（a-r），并通过实验进一步分析了它们对酪氨酸酶的抑制潜力。合成的化合物表现出非常好到中等程度的抑制作用，半数最大抑制浓度在12.40±0.26μM至47.24±1.27μM范围内。在所有衍生物中，5k表现出最高的抑制活性。根据构效关系分析，硫代氨基脲苄基或苯环上带有4-取代基的衍生物对酪氨酸酶表现出更好的抑制潜力。进行了分析（包括ADMET预测和分子对接）并与标准药物（曲酸）进行了比较。这些发现可能有助于寻找食品和化妆品行业可能认为有价值的新型黑色素生成抑制剂。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de66/11378339/5f99ac83815c/d4ra05015k-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de66/11378339/b50914a0b495/d4ra05015k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de66/11378339/47e26083cfdd/d4ra05015k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de66/11378339/39fad92c9855/d4ra05015k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de66/11378339/4cb8393c1975/d4ra05015k-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de66/11378339/40d1e63c79cf/d4ra05015k-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de66/11378339/fcb280a8f623/d4ra05015k-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de66/11378339/5f99ac83815c/d4ra05015k-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de66/11378339/b50914a0b495/d4ra05015k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de66/11378339/47e26083cfdd/d4ra05015k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de66/11378339/39fad92c9855/d4ra05015k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de66/11378339/4cb8393c1975/d4ra05015k-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de66/11378339/40d1e63c79cf/d4ra05015k-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de66/11378339/fcb280a8f623/d4ra05015k-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de66/11378339/5f99ac83815c/d4ra05015k-f6.jpg

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