5-[[3-[(S)-1-Phenyl-2,2,2-trifluoroethoxy]-4-[(S)-2-phenylpropoxy]-phenyl]methylene]-4-oxo-2-thioxo-3-thiazolidineacetic acid

• 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: 5-[[3-[(S)-1-Phenyl-2,2,2-trifluoroethoxy]-4-[(S)-2-phenylpropoxy]-phenyl]methylene]-4-oxo-2-thioxo-3-thiazolidineacetic acid
• 英文别名: 2-[(5Z)-4-oxo-5-[[4-[(2S)-2-phenylpropoxy]-3-[(1S)-2,2,2-trifluoro-1-phenyl-ethoxy]phenyl]methylene]-2-thioxo-thiazolidin-3-yl]acetic acid；2-[(5Z)-4-oxo-5-[[4-[(2S)-2-phenylpropoxy]-3-[(1S)-2,2,2-trifluoro-1-phenylethoxy]phenyl]methylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
• 化学式: C₂₉H₂₄F₃NO₅S₂
• 分子量: 587.64
• InChiKey: LHYRKNFTTKMDNQ-WQFLCVAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3-羧甲基绕丹宁 、 3-[(S)-1-phenyl-2,2,2-trifluoroethoxy]-4-[(S)-2-phenylpropoxy]benzaldehyde 在 ammonium acetate 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 0.25h， 以73%的产率得到5-[[3-[(S)-1-Phenyl-2,2,2-trifluoroethoxy]-4-[(S)-2-phenylpropoxy]-phenyl]methylene]-4-oxo-2-thioxo-3-thiazolidineacetic acid
  参考文献：
  名称：

  Benzylidene thiazolidinediones and their use as antimycotic agents

  摘要：

  公式I的化合物或其盐，其中，A为O或S，X和Y分别代表O、CH2，可以相同也可以不同，Q为(CH2)m—CH(R1)—(CH2)n，R为OR6，NHR8，R1为氢，或者可选择地取代的烷基，R2和R3独立地为氢，或者特定的取代基，但要求R2和R3不同时为H，R4和R5为氢或者特定的取代基，m为0-3；n为0-2；在治疗真菌感染中是有用的。

  公开号：

  US20040006112A1

文献信息

• Benzylidene thiazolidinediones and their use as antimycotic agents
  申请人：Oxford GlycoSciences (UK) Ltd

  公开号：US20040006112A1

  公开（公告）日：2004-01-08

  A compound of formula I or a salt thereof wherein, A is O or S, X and Y independently represent O, CH 2 and may be the same or different, Q is (CH 2 ) m —CH(R1)—(CH 2 ) n , R is OR6, NHR8, R1 is hydrogen, or optionally substituted alkyl, R2 and R3 are independently hydrogen, or specific substituents, provided that R2 and R3 are not both H, and R4 and R5 are hydrogen or specific substituents, m is 0-3; n is 0-2; are useful in the treatment of fungal infections.

  公式I的化合物或其盐，其中，A为O或S，X和Y分别代表O、CH2，可以相同也可以不同，Q为(CH2)m—CH(R1)—(CH2)n，R为OR6，NHR8，R1为氢，或者可选择地取代的烷基，R2和R3独立地为氢，或者特定的取代基，但要求R2和R3不同时为H，R4和R5为氢或者特定的取代基，m为0-3；n为0-2；在治疗真菌感染中是有用的。
• BENZYLIDENE THIAZOLIDINEDIONES AND THEIR USE AS ANTIMYCOTIC AGENTS
  申请人：UCB, S.A.

  公开号：EP1313471B1

  公开（公告）日：2007-04-11
• US7105554B2
  申请人：——

  公开号：US7105554B2

  公开（公告）日：2006-09-12
• [EN] BENZYLIDENE THIAZOLIDINEDIONES AND THEIR USE AS ANTIMYCOTIC AGENTS<br/>[FR] THIAZOLIDINEDIONES DE BENZYLIDENE ET LEUR UTILISATION EN TANT QU'AGENTS ANTIFONGIQUES
  申请人：OXFORD GLYCOSCIENCES UK LTD

  公开号：WO2002017915A1

  公开（公告）日：2002-03-07

  A compound of formula I or a salt thereof wherein, A is O or S, X and Y independently represent O, CH2 and may be the same or different, Q is (CH2)m-CH(R1)-(CH2)n, R is OR6, NHR8, R1 is hydrogen, or optionally substituted alkyl, R2 and R3 are independently hydrogen, or specific substituents, provided that R2 and R3 are not both H, and R4 and R5 are hydrogen or specific substituents, m is 0-3; n is 0-2; are useful in the treatment of fungal infections.
• 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.