(Z)-[5-(4-benzyloxyphenyl)methylidene-4-oxo-2-thioxothiazolidin-3-yl]acetic acid | 1151944-58-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-[5-(4-benzyloxyphenyl)methylidene-4-oxo-2-thioxothiazolidin-3-yl]acetic acid
• 英文别名: 2-(5-(4-(Benzyloxy)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid；2-[(5Z)-4-oxo-5-[(4-phenylmethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
• CAS: 1151944-58-9
• 化学式: C₁₉H₁₅NO₄S₂
• 分子量: 385.464
• InChiKey: KDHQPBOMSXIRRL-YBEGLDIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-苄氧基苯甲醛 、 3-羧甲基绕丹宁 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以76%的产率得到(Z)-[5-(4-benzyloxyphenyl)methylidene-4-oxo-2-thioxothiazolidin-3-yl]acetic acid
  参考文献：
  名称：

  首个布氏锥虫多醇磷酸甘露糖合酶 (DPMS) 的小分子抑制剂，该酶是非洲昏睡病的有效药物靶标

  摘要：

  迫切需要具有抗布氏锥虫活性的类药物分子作为治疗非洲昏睡病的潜在疗法。从已知的其他糖基转移酶抑制剂开始，我们开发了第一个多羟基磷酸甘露糖合酶 (DPMS) 的小分子抑制剂，DPMS 是一种与T. brucei糖复合物生物合成密切相关的甘露糖基转移酶。我们发现这些 DPMS 抑制剂可阻止糖基磷脂酰肌醇 (GPI) 锚的生物合成，并对活锥虫具有杀锥虫活性。

  DOI：

  10.1016/j.bmcl.2009.01.083

文献信息

• In vitro evaluation of 5-arylidene-2-thioxo-4-thiazolidinones active as aldose reductase inhibitors
  作者：Rosanna Maccari、Antonella Del Corso、Marco Giglio、Roberta Moschini、Umberto Mura、Rosaria Ottanà

  DOI：10.1016/j.bmcl.2010.11.041

  日期：2011.1

  2-Thioxo-4-thiazolidinone derivatives were evaluated as aldose reductase inhibitors (ARIs) and most of them exhibited good or excellent in vitro efficacy. Out of the tested compounds, most N-unsubstituted analogues were found to possess inhibitory effects at low micromolar doses and two of them exhibited higher potency than sorbinil, used as a reference drug. The insertion of an acetic chain on N-3 of the thiazolidinone scaffold led to analogues with submicromolar affinity for ALR2 and IC50 values very similar to that of epalrestat, the only ARI currently used in therapy. (C) 2010 Elsevier Ltd. All rights reserved.
• Rhodanine-3-acetic acid derivatives as inhibitors of fungal protein mannosyl transferase 1 (PMT1)
  作者：Michael G Orchard、Judi C Neuss、Carl M.S Galley、Andrew Carr、David W Porter、Phillip Smith、David I.C Scopes、David Haydon、Katherine Vousden、Colin R Stubberfield、Kate Young、Martin Page

  DOI：10.1016/j.bmcl.2004.05.050

  日期：2004.8

  The first inhibitors of fungal protein: mannosyl transferase 1 (PMT1) are described. They are based upon rhodanine-3-acetic acid and several compounds have been identified, for example, 5-[[3-(1-phenylethoxy)-4-(2-phenylethoxy)phenyl]methylene]4-oxo-2-thioxo-3-thiazolidineacetic acid (5a), which inhibit Candida albicans PMT1 with IC(50)s in the range 0.2-0.5 muM. Members of the series are effective in inducing changes in morphology of C. albicans in vitro that have previously been associated with loss of the transferase activity. These compounds could serve as useful tools for studying the effects of protein O-mannosylation and its relevance in the search for novel antifungal agents. (C) 2004 Elsevier Ltd. All rights reserved.
• ANTIMICROBIAL COMPOUNDS AND METHODS FOR USE THEREOF
  申请人：VERSITECH LIMITED

  公开号：US20190307729A1

  公开（公告）日：2019-10-10

  Compounds, pharmaceutical compositions, and methods for treatment of microbial infections are provided. The compounds can potentiate the therapeutic effects of one or more antimicrobial agents when co-administered. The compounds have antivirulence properties. Pharmaceutical compositions including the compounds and a pharmaceutically acceptable carrier are provided. The pharmaceutical composition can further include at least one antibiotic, such as, Gentamicin, amikacin, kanamycin, neomycin, spectinomycin, neamine or any combination thereof. The compounds and compositions can be used to treat or prevent microbial infections.
• [EN] ANTIMICROBIAL COMPOUNDS AND METHODS FOR USE THEREOF<br/>[FR] COMPOSÉS ANTIMICROBIENS ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV HONG KONG

  公开号：WO2017215552A1

  公开（公告）日：2017-12-21

  Compounds, pharmaceutical compositions, and methods for treatment of microbial infections are provided. The compounds can potentiate the therapeutic effects of one or more antimicrobial agents when co-administered. The compounds have antivirulence properties. Pharmaceutical compositions including the compounds and a pharmaceutically acceptable carrier are provided. The pharmaceutical composition can further include at least one antibiotic, such as, Gentamicin, amikacin, kanamycin, neomycin, spectinomycin, neamine or any combination thereof. The compounds and compositions can be used to treat or prevent microbial infections.