(Z)-2-(5-(naphthalen-1-ylmethylene)-2,4-dioxothiazolidin-3-yl)acetic acid | 1039559-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-2-(5-(naphthalen-1-ylmethylene)-2,4-dioxothiazolidin-3-yl)acetic acid
• 英文别名: 2,4-Dioxo-5-(naphthylmethylene)-3-thiazol-idineacetic acid；2-[(5Z)-5-(naphthalen-1-ylmethylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]acetic acid
• CAS: 1039559-06-2
• 化学式: C₁₆H₁₁NO₄S
• 分子量: 313.334
• InChiKey: XSSADKPLSGFAEH-JYRVWZFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-2-(5-(naphthalen-1-ylmethylene)-2,4-dioxothiazolidin-3-yl)acetic acid 在 氯化亚砜 作用下， 反应 1.0h， 生成 (Z)-2-(5-(naphthalen-1-ylmethylene)-2,4-dioxothiazolidin-3-yl)acetyl chloride
  参考文献：
  名称：

  鉴定新型的非羧酸醛糖还原酶抑制剂

  摘要：

  通过用三氟甲基酮部分取代羧基，设计了作为醛糖还原酶（ALR2）抑制剂具有活性的（5-亚芳基-2,4-二氧噻唑并恶唑烷-3-基）乙酸的非羧酸生物甾醇。这些三氟甲基取代的衍生物对ALR2抑制作用的体外评估导致鉴定出两种在低微摩尔剂量下有效的抑制剂。进一步证实，噻唑烷二酮支架的N-3上的羧基是获得最高功效水平的决定性条件。然而，对于与靶酶的相互作用不是必需的，并且可以被不同的极性基团取代，从而获得较少的离子化或工会化的抑制剂。

  DOI：

  10.1016/j.bmc.2010.04.016
• 作为产物：
  描述：

  5-(1'-naphthylidene)-2,4-dioxotetrahydro-1,3-thiazole 在 盐酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 26.0h， 生成 (Z)-2-(5-(naphthalen-1-ylmethylene)-2,4-dioxothiazolidin-3-yl)acetic acid
  参考文献：
  名称：

  Structure–activity relationships and molecular modelling of 5-arylidene-2,4-thiazolidinediones active as aldose reductase inhibitors

  摘要：

  The structure-activity relationships (SARs) of 5-arylidene-2,4-thiazolidinediones active as aldose reductase inhibitors (ARIs) were extended by varying the substitution pattern on the 5-arylidene moiety and on N-3. In particular, the introduction of an additional aromatic ring or an H-bond donor group on the 5-benzylidene ring enhanced ALR2 inhibitory potency. Moreover, the presence of a carboxylic anionic chain on N-3 was shown to be an important, although not essential, structural requisite to produce high levels of ALR2 inhibition. The length of this carboxylic chain was critical and acetic acids 4 were the most effective inhibitors among the tested derivatives. Molecular docking simulations into the ALR2 active site accorded with the in vitro inhibition data. They allowed the rationalization of the observed SARs and provided a pharmacophoric model for this class of ARIs. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.026

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, induced-fit docking investigations, and in vitro aldose reductase inhibitory activity of non-carboxylic acid containing 2,4-thiazolidinedione derivatives
  作者：Rosanna Maccari、Rosaria Ottanà、Rosella Ciurleo、Dietmar Rakowitz、Barbara Matuszczak、Christian Laggner、Thierry Langer

  DOI：10.1016/j.bmc.2008.04.072

  日期：2008.6

  here report a series of non-carboxylic acid containing 2,4-thiazolidinedione derivatives, analogues of previously synthesized carboxylic acids which we had found to be very active in vitro aldose reductase (ALR2) inhibitors. Although the replacement of the carboxylic group with the carboxamide or N-hydroxycarboxamide one decreased the in vitro ALR2 inhibitory effect, this led to the identification

  在继续我们的研究中，我们在这里报告了一系列含有2,4-噻唑烷二酮的非羧酸衍生物，它们是先前合成的羧酸的类似物，我们发现它们在体外是非常有效的醛糖还原酶（ALR2）抑制剂。尽管用羧酰胺或N-羟基羧酰胺取代羧基会降低体外对ALR2的抑制作用，但这导致鉴定出具有微摩尔ALR2亲和力的主要是非电离的衍生物。5-亚芳基部分深刻地影响了这些2，4-噻唑烷二酮的活性。我们的诱导拟合对接研究表明，5-（4-羟基亚苄基）取代的衍生物可能通过去质子化的酚基团结合ALR2活性位点的极性识别区，
• 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。
• 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
• Structure–activity relationships and molecular modelling of 5-arylidene-2,4-thiazolidinediones active as aldose reductase inhibitors
  作者：Rosanna Maccari、Rosaria Ottanà、Carmela Curinga、Maria Gabriella Vigorita、Dietmar Rakowitz、Theodora Steindl、Thierry Langer

  DOI：10.1016/j.bmc.2005.02.026

  日期：2005.4

  The structure-activity relationships (SARs) of 5-arylidene-2,4-thiazolidinediones active as aldose reductase inhibitors (ARIs) were extended by varying the substitution pattern on the 5-arylidene moiety and on N-3. In particular, the introduction of an additional aromatic ring or an H-bond donor group on the 5-benzylidene ring enhanced ALR2 inhibitory potency. Moreover, the presence of a carboxylic anionic chain on N-3 was shown to be an important, although not essential, structural requisite to produce high levels of ALR2 inhibition. The length of this carboxylic chain was critical and acetic acids 4 were the most effective inhibitors among the tested derivatives. Molecular docking simulations into the ALR2 active site accorded with the in vitro inhibition data. They allowed the rationalization of the observed SARs and provided a pharmacophoric model for this class of ARIs. (c) 2005 Elsevier Ltd. All rights reserved.