(Z)-2-(benzo[d]thiazol-2-ylamino)-5-(4-hydroxy-3-methoxybenzylidene)thiazol-4(5H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (Z)-2-(benzo[d]thiazol-2-ylamino)-5-(4-hydroxy-3-methoxybenzylidene)thiazol-4(5H)-one
• 英文别名: (Z)-2-(benzo[d]thiazol-2-ylamino)-5-(4-hydroxy-3-methoxybenzylidene)thiazole-4(5H)-one；(5Z)-2-(1,3-benzothiazol-2-ylimino)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
• 化学式: C₁₈H₁₃N₃O₃S₂
• 分子量: 383.452
• InChiKey: NLWNNVRLHHHKAK-DHDCSXOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  137
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  香草醛 、 2-benzothiazol-2-ylamino-thiazol-4-one 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 17.0h， 以73.6%的产率得到(Z)-2-(benzo[d]thiazol-2-ylamino)-5-(4-hydroxy-3-methoxybenzylidene)thiazol-4(5H)-one
  参考文献：
  名称：

  (<i>Z</i>)-2-(Benzo[<i>d</i>]thiazol-2-ylamino)-5-(substituted benzylidene)thiazol-4(5<i>H</i>)-one Derivatives as Novel Tyrosinase Inhibitors

  摘要：

  抑制酪氨酸酶是防止黑色素在皮肤中积聚，从而抑制色素沉着病的一个重要目标。因此，酪氨酸酶抑制剂是化妆品和色素沉着疾病治疗中一个极具吸引力的目标。然而，由于酪氨酸酶抑制剂对皮肤有毒性或缺乏选择性和稳定性，目前只有少数几种酪氨酸酶抑制剂可供选择。在这里，我们新合成了 13 种 (Z)-2-(benzo[d]thiazol-2-ylamino)-5-(substituted benzylidene)thiazol-4(5H)-one 衍生物，并考察了它们对黑色素生成的影响。在这些化合物中，MHY2081 对 B16F10 黑色素瘤细胞中的酪氨酸酶具有最强的抑制作用，且无细胞毒性。同样，MHY2081 处理后黑色素生成明显减少。对接模拟显示，与著名的竞争性酪氨酸酶抑制剂曲酸相比，MHY2081与酪氨酸酶形成氢键和芳香族相互作用，与酪氨酸酶的亲和力更强，与酪氨酸酶的残基形成三个氢键和疏水相互作用。与此同时，Lineweaver-Burk plot 分析表明 MHY2081 是酪氨酸酶的强竞争性抑制剂。总之，MHY2081 可能是一种新型的酪氨酸酶抑制剂，可用于色素沉着疾病的预防和治疗。

  DOI：

  10.1248/bpb.b15-00300

文献信息

• 피부미백 활성을 갖는 신규 화합물 및 이의 의학적 용도
  申请人：Pusan National University Industry-University Cooperation Foundation 부산대학교 산학협력단(220040044843) BRN ▼621-82-06530

  公开号：KR101677121B1

  公开（公告）日：2016-11-30

  본 발명은 피부미백 활성을 갖는 신규 화합물 및 이의 의학적 용도에 관한 것으로, 본 발명에 따른 화합물들은 널리 알려진 미백제인 코지산보다 탁월하게 타이로시네이즈를 억제하는 피부미백 활성을 지니므로 피부미백용 약학조성물, 화장품 또는 건강식품에 유용하게 사용될 수 있다.

  This invention relates to novel compounds with skin whitening activity and their medical uses. The compounds according to the invention have superior skin whitening activity by inhibiting tyrosinase more effectively than the well-known whitening agent, kojic acid. Therefore, the compounds can be used beneficially in pharmaceutical compositions for skin whitening, cosmetics, or health supplements.
• 2-Heteroarylimino-5-benzylidene-4-thiazolidinones analogues of 2-thiazolylimino-5-benzylidene-4-thiazolidinones with antimicrobial activity: Synthesis and structure–activity relationship
  作者：Paola Vicini、Athina Geronikaki、Matteo Incerti、Franca Zani、John Dearden、Mark Hewitt

  DOI：10.1016/j.bmc.2008.02.001

  日期：2008.4.1

  2-Heteroarylimino-5-benzylidene-4-thiazolidinones, unsubstituted or carrying hydroxy, methoxy, nitro and chloro groups on the benzene ring, were synthesised and assayed in vitro for their antimicrobial activity against Gram positive and Gram negative bacteria, yeasts and mould. The antimicrobial activity of the 2-benzo[d] thiazolyl-and of the 2-benzo[d] isothiazolyl-imino-5-benzylidene- 4-thiazolidinones is, on the whole, lower in comparison with the high activity detected for the derivatives of the 2-thiazolylimino5- benzylidene-4-thiazolidinone class. Nevertheless most of the benzo[d] thiazole analogues display good inhibition of the growth of Gram positive bacilli and staphylococci, including methicillin-resistant Staphylococcus strains. Among the 2-benzo[d] isothiazole analogues a few derivatives show a strong and selective activity against bacilli. Moreover, it is worth noting that the replacement of the thiazole nucleus for the benzo[d] thiazole bicyclic system in the parent 2-(benzo[d] thiazol-2-ylimino) thiazolidin-4-one leads to significant antifungal properties against both yeasts and moulds, properties not shown by the analogous 2-thiazolyl-and 2-benzo[d] isothiazolyl-imino) thiazolidin-4-ones. The structure-activity relationship of 33 analogues possessing the 2-heteroarylimino-4- thiazolidinone structure is analysed through QSAR models. (C) 2008 Elsevier Ltd. All rights reserved.