(Z)-3-ethyl-5-(naphthalen-1-ylmethylene)-2-thioxothiazolidin-4-one | 1220624-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-3-ethyl-5-(naphthalen-1-ylmethylene)-2-thioxothiazolidin-4-one
• 英文别名: (5Z)-3-ethyl-5-(naphthalen-1-ylmethylidene)-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 1220624-86-1
• 化学式: C₁₆H₁₃NOS₂
• 分子量: 299.417
• InChiKey: NQCJVKCITQKLQV-UVTDQMKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-乙基-2-硫代-4-噻唑烷二酮 、 1-萘甲醛 在 sodium acetate 、 溶剂黄146 作用下， 反应 16.0h， 以31%的产率得到(Z)-3-ethyl-5-(naphthalen-1-ylmethylene)-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  Exploration of inhibitors for diaminopimelate aminotransferase

  摘要：

  Bacteria and higher plants make L-lysine from diaminopimelic acid (DAP). In mammals L-lysine is an essential amino acid that must be acquired from the diet as the biosynthetic pathway is absent for this key constituent of proteins. Recently, LL-diaminopimelate aminotransferase (LL-DAP-AT), a pyridoxal-5'-phosphate (PLP)-dependent enzyme, was reported to catalyze a key step in the route to L-lysine in plants and Chlamydia. Specific inhibitors of this enzyme could thus potentially serve as herbicides or antibiotics that are non-toxic to mammals. In this work, 29,201 inhibitors were screened against LL-DAP-AT and the IC50 values were determined for the top 46 compounds. An aryl hydrazide and rhodanine derivatives were further modified to generate 20 analogues that were also tested against LL-DAP-AT. These analogues provide additional structure-activity relationships (SAR) that are useful in guiding further design of inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.001

文献信息

• [EN] PYRROLIDINE DERIVATIVE, AND PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING BETA-AMYLOID OR TAU PROTEIN-ASSOCIATED DISEASES CONTAINING SAME<br/>[FR] DÉRIVÉ DE PYRROLIDINE ET COMPOSITION PHARMACEUTIQUE DE PRÉVENTION OU DE TRAITEMENT DE MALADIES ASSOCIÉES À LA PROTÉINE BÊTA-AMYLOÏDE OU TAU CONTENANT CE DERNIER<br/>[KO] 피롤리딘 유도체 및 이를 포함하는 베타-아밀로이드 또는 타우 단백질 관련 질병의 예방 또는 치료용 약학 조성물
  申请人：YONSEI UNIV UNIV INDUSTRY FOUNDATION UIF

  公开号：WO2021133037A1

  公开（公告）日：2021-07-01

  신규한 피롤리딘 유도체 또는 이의 약학적으로 허용 가능한 염, 및 이를 포함하는 베타-아밀로이드 및/또는 타우 단백질의 응집 억제 및/또는 베타-아밀로이드 및/또는 타우 단백질의 응집체 분해, 및/또는 베타-아밀로이드 및/또는 타우 단백질 관련 질병의 예방 및/또는 치료 효과를 갖는 약학 조성물이 제공된다.
• Exploration of inhibitors for diaminopimelate aminotransferase
  作者：Chenguang Fan、Matthew D. Clay、Michael K. Deyholos、John C. Vederas

  DOI：10.1016/j.bmc.2010.02.001

  日期：2010.3

  Bacteria and higher plants make L-lysine from diaminopimelic acid (DAP). In mammals L-lysine is an essential amino acid that must be acquired from the diet as the biosynthetic pathway is absent for this key constituent of proteins. Recently, LL-diaminopimelate aminotransferase (LL-DAP-AT), a pyridoxal-5'-phosphate (PLP)-dependent enzyme, was reported to catalyze a key step in the route to L-lysine in plants and Chlamydia. Specific inhibitors of this enzyme could thus potentially serve as herbicides or antibiotics that are non-toxic to mammals. In this work, 29,201 inhibitors were screened against LL-DAP-AT and the IC50 values were determined for the top 46 compounds. An aryl hydrazide and rhodanine derivatives were further modified to generate 20 analogues that were also tested against LL-DAP-AT. These analogues provide additional structure-activity relationships (SAR) that are useful in guiding further design of inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.