N-(3,4-二氯苯基)丙二酸 | 17722-36-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(3,4-二氯苯基)丙二酸
• 英文名称: 3-(3,4-dichloroanilino)-3-oxopropanoic acid
• 英文别名: N-(3,4-dichlorophenyl)malonamic acid；N-Malonyl-3,4-dichloroaniline；DCOPA；α-(3,4-Dichlor-phenylcarbamoyl)-essigsaeure
• CAS: 17722-36-0
• 化学式: C₉H₇Cl₂NO₃
• 分子量: 248.065
• InChiKey: JEFJREKVJYACNK-UHFFFAOYSA-N

物化性质

• 熔点：
  131 °C
• 沸点：
  498.4±45.0 °C(Predicted)
• 密度：
  1.574±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-5-(p-chlorophenylazo)benzaldehyde 、 N-(3,4-二氯苯基)丙二酸 在 吡啶 作用下， 反应 0.1h， 以77.86%的产率得到6-[2-(4-chlorophenyl)diazenyl]-N-(3,4-dichlorophenyl)-2-oxo-2H-chromene-3-carboxamide
  参考文献：
  名称：

  Shahnawaaz, Mohammed; Naqvi, Arshi; Rao, Arikatla V., Asian Journal of Chemistry, 2010, vol. 22, # 7, p. 5781 - 5783

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(3,4-二氯苯胺基)-3-氧代丙酸乙酯 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 N-(3,4-二氯苯基)丙二酸
  参考文献：
  名称：

  1,2,3,4-四氢喹啉-2,3,4-三酮3-肟的合成与构效关系：NMDA受体甘氨酸位点的新型高效拮抗剂。

  摘要：

  合成了一系列的1,2,3,4-四氢喹啉-2,3,4-三酮3-肟（QTO），并评估了其对NMDA受体甘氨酸位点的拮抗作用。使用[3H] DCKA结合测定法在大鼠脑膜中和在表达克隆的大鼠NMDA受体1a / 2C亚基的非洲爪蟾卵母细胞中通过电生理学测定甘氨酸位点亲和力。还分析了所选化合物对表达大鼠脑聚-（A）+ RNA的爪蟾卵母细胞中AMPA受体的拮抗作用。通过将2，4-喹啉二醇亚硝化来制备QTO。结构活性研究表明，在5、6和7位上的取代会增加效力，而在8位上的取代会导致效力降低。在评估的衍生工具中，有5,6，7-trichloro-QTO是最有效的拮抗剂，在[3H] DCKA结合试验中，IC50为7 nM，非洲爪蟾卵母细胞中表达的NMDA受体的Kb为1-2 nM。在电生理测定中，5,6,7-Trichloro-QTO对AMPA受体的Kb也为180 nM。将QTO的SAR与1,4-二氢喹喔啉-2

  DOI：

  10.1021/jm960214k

文献信息

• Bisubstituted carbocyclic cyclophilin binding compounds and their use
  申请人：——

  公开号：US20020127605A1

  公开（公告）日：2002-09-12

  The present invention relates to novel, non-peptidic small organic compounds having an affinity for cyclophilin (CyP)-type immunophilin proteins. In the compounds of this invention, at least two carbo- or heterocyclic groups are attached to a central saturated, partially saturated, or aromatic 5-6 membered carbocyclic ring by a combination of straight or branched linker chains. The invention further relates to pharmaceutical compositions comprising one or more of the said compounds, and to the uses of these compounds and compositions for binding CyP-type proteins, inhibiting their peptidyl-prolyl isomerase activity, and for research, development, and therapeutic applications in a variety of medical disorders, such as neurological disorders, hair loss disorders, ischemic disorders, and disorders caused by viral or protozoan infection.

  本发明涉及一种新型的非肽类小有机化合物，具有与环存肥蛋白（CyP）型免疫蛋白亲和力。在本发明的化合物中，至少有两个碳环或杂环基团通过直链或支链连接到一个中央的饱和、部分饱和或芳香性的5-6环碳环上。本发明还涉及包含所述化合物中的一个或多个的制药组合物，并且用于结合CyP型蛋白，抑制其肽基-脯氨酰异构酶活性，以及在各种医学疾病中进行研究、开发和治疗应用，例如神经系统疾病、脱发疾病、缺血性疾病和由病毒或原虫感染引起的疾病。
• Water Soluble Haloanilide Calcium-Release Calcium Channel Inhibitory Compounds and Methods to Control Bone Erosion and Inflammation Associated with Arthritides
  申请人：West Virginia University

  公开号：US20170260128A1

  公开（公告）日：2017-09-14

  A compound that is selected from the group consisting of 3-(3,4-dichloroanilino)-3-oxopropanoic acid (hereinafter “DCOPA”); N-methyl-DCOPA; N,2-dimethyl-DCOPA; 2-methyl-DCOPA; isobutyl-DCOPA; N-methyl-isobutyl DCOPA; 3-(3,4-bibromoanilino)-3-oxopropanoic acid; and analogs of DCOPA; and analogs of 3-(3,4-bibromoanilino)-3-oxopropanoic acid; and pharmaceutically acceptable salts of these compounds, are disclosed. A method of controlling bone erosion in a patient comprising administering to the patient a therapeutically effective amount of at least one of these compounds, or a pharmaceutically acceptable salt of at least one of these compounds, is provided. A method of reducing inflammation in a patient having an inflammatory condition comprising administering to the patient a therapeutically effective amount of at least one of these compounds, or a pharmaceutically acceptable salt of at least one of these compounds is provided.

  所披露的化合物选自以下组：3-(3,4-二氯苯胺基)-3-氧代丙酸（以下简称“DCOPA”）；N-甲基-DCOPA；N,2-二甲基-DCOPA；2-甲基-DCOPA；异丁基-DCOPA；N-甲基-异丁基-DCOPA；3-(3,4-二溴苯胺基)-3-氧代丙酸；以及DCOPA的类似物；以及3-(3,4-二溴苯胺基)-3-氧代丙酸的类似物；以及这些化合物的药学上可接受的盐。提供了一种控制患者骨质侵蚀的方法，包括向患者施用至少一种这些化合物的治疗有效量，或至少一种这些化合物的药学上可接受的盐。提供了一种减少患有炎症症状的患者炎症的方法，包括向患者施用至少一种这些化合物的治疗有效量，或至少一种这些化合物的药学上可接受的盐。
• A Convenient one-pot synthesis of n-arylmalonamic acid via in-situ generation of malonyl monoacyl chloride
  作者：Hsiencheng Shih、Gary O Rankin

  DOI：10.1080/00397919608086760

  日期：1996.2

  Abstract A convenient one-pot synthesis of N-arylmalonamic acid has been demonstrated based on the in-situ generation ofmalonyl monoacyl chloride, followed by reaction with aniline.

  摘要 基于丙二酰单酰氯的原位生成，然后与苯胺反应，已经证明了一种方便的 N-芳基丙二酸的一锅法合成。
• Tackling <i>Pseudomonas aeruginosa</i> Virulence by a Hydroxamic Acid-Based LasB Inhibitor
  作者：Andreas M. Kany、Asfandyar Sikandar、Samir Yahiaoui、Jörg Haupenthal、Isabell Walter、Martin Empting、Jesko Köhnke、Rolf W. Hartmann

  DOI：10.1021/acschembio.8b00257

  日期：2018.9.21

  highly selective thiol scaffold. Using X-ray crystallography, the lack of inhibition of a range of human matrix metalloproteases could be attributed to a distinct binding mode sparing the S1′ pocket. The inhibitor was shown to restore the effect of the antimicrobial peptide LL-37, decrease the formation of P. aeruginosa biofilm and, for the first time for a LasB inhibitor, reduce the release of extracellular

  为了寻找新的抗生素来对抗耐药性病原体的挑战性传播，细菌蛋白酶代表了致病阻断剂发展的有希望的目标。蛋白酶抑制剂的常见基序是异羟肟酸功能，然而该组常常与各种金属蛋白酶的非特异性抑制有关。在这项工作中，抑制铜绿假单胞菌分泌的有害锌金属蛋白酶LasB通过异羟肟酸酯衍生物进行了描述。本抑制剂是基于最近报道的高选择性硫醇骨架而开发的。使用X射线晶体学，缺乏对一系列人类基质金属蛋白酶的抑制作用可归因于保留S1'口袋的独特结合模式。该抑制剂被证明可以恢复抗菌肽LL-37的作用，减少铜绿假单胞菌生物膜的形成，并且对于LasB抑制剂而言，这是首次减少细胞外DNA的释放。因此，它能够破坏几种重要的细菌抗性机制。这些结果突出了蛋白酶抑制剂对抗细菌感染的潜力，并指出了即使使用强锌锚定剂也可以实现选择性抑制的可能性。
• 3,4-Dichloroaniline is detoxified and exported via different pathways in Arabidopsis and soybean
  作者：Si-Houy Lao、Caroline Loutre、Melissa Brazier、Julian O.D Coleman、David J Cole、Robert Edwards、Frederica L Theodoulou

  DOI：10.1016/s0031-9422(03)00289-9

  日期：2003.7

  The metabolic fate of [UL-C-14]-3,4-dichloroaniline (DCA) was investigated in Arabidopsis root cultures and soybean plants over a 48 h period following treatment via the root media. DCA was rapidly taken up by both species and metabolised, predominantly to N-malonyl-DCA in soybean and N-glucosyl-DCA in Arabidopsis. Synthesis occurred in the roots and the respective conjugates were largely exported into the culture medium, a smaller proportion being retained within the plant tissue. Once conjugated, the DCA metabolites in the medium were not then readily taken up by roots of either species. The difference in the routes of DCA detoxification in the two plants could be explained partly by the relative activities of the respective conjugating enzymes, soybean containing high DCA-N-malonyltransferase activity, while in Arabidopsis DCA-N-glucosyltransferase activity predominated. A pre-treatment of plants with DCA increased DCA-N-malonyltransferase activity in soybean but not in Arabidopsis, indicating differential regulation of this enzyme in the two plant species. This study demonstrates that DCA can undergo two distinct detoxification mechanisms which both lead to the export of conjugated, metabolites from roots into the surrounding medium in contrast to the vacuolar deposition more commonly associated with the metabolism of xenobiotics in plants. (C) 2003 Elsevier Ltd. All rights reserved.