1-(3,4-二氯苯基)-2-氧代吡咯烷-4-羧酸 | 91064-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-(3,4-二氯苯基)-2-氧代吡咯烷-4-羧酸
• 中文别名: 1-(3,4-二氯苯基)-2-氧吡咯烷-4-羧酸
• 英文名称: 1-(3,4-dichlorophenyl)-5-oxopyrrolidine-3-carboxylic acid
• 英文别名: 1-(3,4-dichlorophenyl)-5-pyrrolidone-3-carboxylic acid；1-(3,4-Dichlorophenyl)-2-oxopyrrolidine-4-carboxylic acid
• CAS: 91064-25-4
• 化学式: C₁₁H₉Cl₂NO₃
• mdl: MFCD00665764
• 分子量: 274.103
• InChiKey: WMACFMOMYRKMOJ-UHFFFAOYSA-N

物化性质

• 熔点：
  139-142 °C(Solv: ethanol (64-17-5))
• 沸点：
  580.6±50.0 °C(Predicted)
• 密度：
  1.552±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933790090

SDS

1-(3,4-二氯苯基)-2-氧代吡咯烷-4-羧酸MSDS英文版

反应信息

• 作为反应物：
  描述：

  1-(3,4-二氯苯基)-2-氧代吡咯烷-4-羧酸 在 甲醇 、 sodium tetrahydroborate 、 硫酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [1-(3,4-Dichlorophenyl)-5-oxopyrrolidin-3-yl]methyl methanesulfonate
  参考文献：
  名称：

  Synthesis of 4-[1-(substituted phenyl)-2-oxo-pyrrolidin-4-yl]methyloxybenzoic acids and related compounds, and their inhibitory capacities toward fatty-acid and sterol biosyntheses

  摘要：

  The synthesis of a series of 4[1-(substituted phenyl)-2-oxo-pyrrolidin-4-yl]methyloxybenzoic acids and related compounds, and their evaluation for inhibitory capacity toward fatty-acid and sterol biosyntheses using rats' liver slices in vitro and rabbits in vivo, are described. Among the compounds synthesized, 7e, 7g, 7h, 7i, 7k, 7r, 21, 23 and 29a b showed a potent inhibitory activity toward fatty-acid and sterol biosyntheses. Their IC(50)s were 4.4-6.8 x 10(-6) M and 6.6-9.8 x 10(-6) M, respectively. These activities were always superior to those of compounds I, II, III and Clinofibrate as references. The inhibitory activity toward the sterol biosynthesis of these compounds was inferior to that of Pravastatin. The reducing effects of the representative compounds (7e and 7l) toward plasma cholesterols and triglyceride were evaluated in Japanese white rabbits (30 and 100 mg/kg, po) and compared with those of Clinofibrate:and Pravastatin; The compounds showed a similar hypocholesterolemic effect to Pravastatin and a more potent hypotriglycemic effect than Clinofibrate and Pravastatin in this animal model. Thus, a dual,action of hypolipidemic effects was noted in 7e and 7l compared with the references.

  DOI：

  10.1016/0223-5234(94)90029-9
• 作为产物：
  描述：

  衣康酸 、 3,4-二氯苯胺 以94%的产率得到1-(3,4-二氯苯基)-2-氧代吡咯烷-4-羧酸
  参考文献：
  名称：

  发现具有潜在诱导的系统抗性的新型植物活化剂和支架：从茉莉酸到吡咯烷酮†

  摘要：

  由于病原体，昆虫和某些特定微生物的感染，或者经过特定化学物质的处理，植物会发展出多方面的系统抗性。1其中，系统性获得性抵抗力（SAR）和诱导性系统抵抗力（ISR）2是两个最重要的类型。为了激活它们，已经基于SA途径开发了大量化学诱导剂。但是，对于新的植物激活剂，很少研究JA途径。在这项研究中，从JA及其类似物出发，基于分子三维形状和药效基团相似性比较（SHAFTS），预测了一种新的先导化合物吡咯烷酮，它将作为一种植物激活剂的新支架，并形成一系列1-苯基设计并合成了-5-吡咯烷酮-3-羧酸衍生物。对生物活性进行了评估，大多数化合物均显示出令人满意的活性。特别是化合物7-11在体外几乎没有显示 活性，但对被测疾病具有优异的疗效，并证实了虚拟筛选结果的预测，这促进了SHAFTS在农药开发中的应用。

  DOI：

  10.1039/c6md00261g

文献信息

• The discovery of new plant activators and scaffolds with potential induced systemic resistance: from jasmonic acid to pyrrolidone
  作者：Kang Chang、Yanxia Shi、Jianqin Chen、Zenghui He、Zheng Xu、Zhenjiang Zhao、Weiping Zhu、Honglin Li、Yufang Xu、BaoJu Li、Xuhong Qian

  DOI：10.1039/c6md00261g

  日期：——

  the JA pathway was rarely investigated for new plant activators. In this study, starting from JA and its analogs, based on the molecular three-dimensional shape and pharmacophore similarity comparison (SHAFTS), a new lead compound, pyrrolidone, as a new scaffold of plant activators was predicted and a series of 1-phenyl-5-pyrrolidone-3-carboxylic acid derivatives were designed and synthesized. The

  由于病原体，昆虫和某些特定微生物的感染，或者经过特定化学物质的处理，植物会发展出多方面的系统抗性。1其中，系统性获得性抵抗力（SAR）和诱导性系统抵抗力（ISR）2是两个最重要的类型。为了激活它们，已经基于SA途径开发了大量化学诱导剂。但是，对于新的植物激活剂，很少研究JA途径。在这项研究中，从JA及其类似物出发，基于分子三维形状和药效基团相似性比较（SHAFTS），预测了一种新的先导化合物吡咯烷酮，它将作为一种植物激活剂的新支架，并形成一系列1-苯基设计并合成了-5-吡咯烷酮-3-羧酸衍生物。对生物活性进行了评估，大多数化合物均显示出令人满意的活性。特别是化合物7-11在体外几乎没有显示 活性，但对被测疾病具有优异的疗效，并证实了虚拟筛选结果的预测，这促进了SHAFTS在农药开发中的应用。
• Application of a Parallel Synthetic Strategy in the Discovery of Biaryl Acyl Sulfonamides as Efficient and Selective Na_V1.7 Inhibitors
  作者：Erin F. DiMauro、Stephen Altmann、Loren M. Berry、Howard Bregman、Nagasree Chakka、Margaret Chu-Moyer、Elma Feric Bojic、Robert S. Foti、Robert Fremeau、Hua Gao、Hakan Gunaydin、Angel Guzman-Perez、Brian E. Hall、Hongbing Huang、Michael Jarosh、Thomas Kornecook、Josie Lee、Joseph Ligutti、Dong Liu、Bryan D. Moyer、Daniel Ortuno、Paul E. Rose、Laurie B. Schenkel、Kristin Taborn、Jean Wang、Yan Wang、Violeta Yu、Matthew M. Weiss

  DOI：10.1021/acs.jmedchem.6b00425

  日期：2016.9.8

  a parallel synthetic approach was applied to rapidly generate the derived acyl sulfonamides. A biaryl acyl sulfonamide hit from this library was elaborated, optimizing for potency and selectivity with attention to physicochemical properties. The resulting novel leads are potent, ligand and lipophilic efficient, and selective over hNaV1.5. Representative lead 36 demonstrates selectivity over other human

  大多数有效的和选择性的hNa V 1.7抑制剂具有常见的药理学特征，包括杂芳基磺酰胺头基和亲脂性芳族尾基。最近，已经出现了类似的芳香族尾基与酰基磺酰胺头基结合的报道，酰基磺酰胺赋予了相对于hNa V的选择性水平1.5与杂芳基磺酰胺相当。从满足亲脂性尾部中选定药理学要求的市售羧酸开始，采用平行合成方法快速生成衍生的酰基磺酰胺。精心制作了该文库中的联芳基酰基磺酰胺，优化了效价和选择性，并关注了理化性质。所得的新的铅是有效的，配体和亲脂性的，并且在hNa V 1.5上具有选择性。代表性的铅36证明了在鼠类中对其他人类Na V同工型的选择性和良好的药代动力学。与已知的杂芳基磺酰胺抑制剂相比，本文报道的联芳基酰基磺酰胺还可以提供ADME优势。
• N-Aryl pyrrolidinonyl oxadiazoles as potent mGluR5 positive allosteric modulators
  作者：Mathivanan Packiarajan、Christine G. Mazza Ferreira、Sang-Phyo Hong、Andrew D. White、Gamini Chandrasena、Xiaosui Pu、Robbin M. Brodbeck、Albert J. Robichaud

  DOI：10.1016/j.bmcl.2012.06.094

  日期：2012.9

  A novel series of N-aryl pyrrolidinonyl oxadiazoles were identified as mGluR5 positive allosteric modulators (PAMs). Optimization of the initial lead compound 6a led to the identification of the 12c (-) enantiomer as a potent compound with acceptable in vitro clearance, CYP, hERG and PK properties. Para substituted N-aryl pyrrolidinonyl oxadiazoles are mGluR5 PAMs while the meta and ortho substituted N-aryl pyrrolidinonyl oxadiazoles are negative allosteric modulators (NAMs). Para fluoro substitution on the N-aryl group and meta chloro or methyl substituents on the aryl oxadiazole moiety are optimal for mGluR5 PAM efficacy. The existence of an exquisitely sensitive 'PAM to NAM switch' within this chemotype making it challenging for simultaneous optimization of potency and drug-like properties. (C) 2012 Elsevier Ltd. All rights reserved.
• Sodium borohydride–iodine mediated reduction of γ-lactam carboxylic acids followed by DDQ mediated oxidative aromatisation: a simple approach towards N-aryl-formylpyrroles and 1,3-diaryl-formylpyrroles
  作者：Pranab Haldar、Gopa Barman、Jayanta K. Ray

  DOI：10.1016/j.tet.2007.01.058

  日期：2007.4

  A simple methodology for the conversion of substituted N-aryl-gamma-lactam 2/3-carboxylic acids to substituted N-aryl-2/3-formyl-pyrroles has been developed. Several N-aryl-gamma-lactam 2/3-carboxylic acids were reduced to substituted (N-aryl-pyrroliden-2/3-yl)-methanols in good yields by using the NaBH4-I-2 system. Aromatisation and in situ oxidation of these alcohols using DDQ produced N-aryl-2/3-formyl-pyrroles, which act as key starting material and intermediates in the synthesis of several bioactive compounds. (c) 2007 Elsevier Ltd. All rights reserved.
• A novel access to bisformylated pyrroles via decarboxylation of N-aryl-γ-lactam-carboxylic acids under Vilsmeier reaction conditions
  作者：Gopa Barman、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2009.11.005

  日期：2010.1

  A simple methodology for the conversion of substituted N-aryl-gamma-lactam 2/3-carboxylic acids to substituted N-aryl-diformylated pyrroles has been developed. Several gamma-lactam 2/3-carboxylic acids were subjected to Vilsmeier reagent and substituted diformylated pyrroles are isolated in one-step process. (C) 2009 Elsevier Ltd. All rights reserved.