(Z)-2-(5-(2-chlorobenzylidene)-2,4-dioxothiazolidin-3-yl)acetic acid | 1452759-66-8

• 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)-2-(5-(2-chlorobenzylidene)-2,4-dioxothiazolidin-3-yl)acetic acid
• 英文别名: [5-(2-Chlorobenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]acetic acid；2-[(5Z)-5-[(2-chlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetic acid
• CAS: 1452759-66-8
• 化学式: C₁₂H₈ClNO₄S
• 分子量: 297.719
• InChiKey: XXDBEXHBCCCONV-UITAMQMPSA-N

物化性质

• 沸点：
  509.9±60.0 °C(Predicted)
• 密度：
  1.616±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 2-(2,4-dioxothiazolidin-3-yl)acetate 在 哌啶 、 盐酸 、 溶剂黄146 作用下， 以 水 、 甲苯 为溶剂， 反应 18.0h， 生成 (Z)-2-(5-(2-chlorobenzylidene)-2,4-dioxothiazolidin-3-yl)acetic acid
  参考文献：
  名称：

  2,4-噻唑烷二酮类和类似杂环作为二氢吡啶二羧酸合酶抑制剂的合成及构效关系研究

  摘要：

  二氢吡啶二羧酸合酶 (DHDPS) 负责赖氨酸生物合成的二氨基庚二酸途径的第一步，已成为开发新的抗菌和除草剂的有吸引力的目标。在此，我们报告了第一个大肠杆菌DHDPS抑制剂的发现和探索，这些抑制剂已从筛选先导中鉴定出来，而不是基于赖氨酸生物合成途径的底物。已经制备了超过 50 种噻唑烷二酮和相关类似物，以彻底评估针对这种具有重要意义的酶的构效关系。

  DOI：

  10.1016/j.bmc.2021.116518

文献信息

• [EN] HETEROCYCLIC INHIBITORS OF LYSINE BIOSYNTHESIS VIA THE DIAMINOPIMELATE PATHWAY<br/>[FR] INHIBITEURS HÉTÉROCYCLIQUES DE LA BIOSYNTHÈSE DE LA LYSINE PAR L'INTERMÉDIAIRE DE LA VOIE DIAMINOPIMÉLATE
  申请人：UNIV LA TROBE

  公开号：WO2018187845A1

  公开（公告）日：2018-10-18

  The present invention relates to certain heterocyclic compounds of formula (1) that have the ability to inhibit lysine biosynthesis via the diaminopimelate biosynthesis pathway in certain organisms. As a result of this activity these compounds can be used in applications where inhibition of lysine biosynthesis is useful. Applications of this type include the use of the compounds as herbicides.

  本发明涉及具有以下公式（1）的某些杂环化合物，这些化合物能够通过某些生物体中的二氨基戊二酸生物合成途径抑制赖氨酸的生物合成。由于这种活性，这些化合物可以用于需要抑制赖氨酸生物合成的应用中。这类应用包括将这些化合物用作除草剂。
• Synthesis, characterization, and biological evaluation of thiazolidine-2,4-dione derivatives
  作者：Shankar G. Alegaon、Kallanagouda R. Alagawadi、Sneha M. Pawar、D. Vinod、Udaysingh Rajput

  DOI：10.1007/s00044-013-0705-2

  日期：2014.2

  As a part of our continuation studies in developing new derivatives as dual antimicrobial/antitumor agents we describe the synthesis of new (Z)-2-(5-arylidene-2,4-dioxothiazolidin-3-yl) acetic acid derivatives (3a-m). The chemical structures of the compound were elucidated by FTIR, H-1 NMR, C-13 NMR, and elemental analysis data. The antimicrobial activity of all products was examined. All newly synthesized compounds were tested for their in vitro anticancer activity against four cancer cell lines. Among the synthesized compounds, 3a exhibited notable activity against HeLa, HT29, A549, and MCF-7 cell lines with IC50 values of 55, 40, 38, and 50 mu M, respectively. In order to predict the drug likeliness of the synthesized compounds on the guidelines of Lipinski rule of five studies was carried out using Pallas software.
• HETEROCYCLIC INHIBITORS OF LYSINE BIOSYNTHESIS VIA THE DIAMINOPIMELATE PATHWAY
  申请人：La Trobe University

  公开号：EP3609494A1

  公开（公告）日：2020-02-19
• Synthesis and structure-activity relationship studies of 2,4-thiazolidinediones and analogous heterocycles as inhibitors of dihydrodipicolinate synthase
  作者：Rebecca M. Christoff、Tatiana P. Soares da Costa、Saadi Bayat、Jessica K. Holien、Matthew A. Perugini、Belinda M. Abbott

  DOI：10.1016/j.bmc.2021.116518

  日期：2021.12

  antibacterial and herbicidal agents. Herein, we report the discovery and exploration of the first inhibitors of E. coli DHDPS which have been identified from screening lead and are not based on substrates from the lysine biosynthesis pathway. Over 50 thiazolidinediones and related analogues have been prepared in order to thoroughly evaluate the structure-activity relationships against this enzyme of significant

  二氢吡啶二羧酸合酶 (DHDPS) 负责赖氨酸生物合成的二氨基庚二酸途径的第一步，已成为开发新的抗菌和除草剂的有吸引力的目标。在此，我们报告了第一个大肠杆菌DHDPS抑制剂的发现和探索，这些抑制剂已从筛选先导中鉴定出来，而不是基于赖氨酸生物合成途径的底物。已经制备了超过 50 种噻唑烷二酮和相关类似物，以彻底评估针对这种具有重要意义的酶的构效关系。