4-(4-氯苄基氨基)-3-氨基苯甲酸甲酯 | 174422-23-2

• 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: 4-(4-氯苄基氨基)-3-氨基苯甲酸甲酯
• 英文名称: methyl 3-amino-4-(4-chlorobenzyl)aminobenzoate
• 英文别名: methyl 3-amino-4-(p-chlorobenzylamino)benzoate；methyl 3-amino-4-{[(4-chlorophenyl)methyl]amino}benzoate；methyl 3-amino-4-[(4-chlorophenyl)methylamino]benzoate
• CAS: 174422-23-2
• 化学式: C₁₅H₁₅ClN₂O₂
• 分子量: 290.749
• InChiKey: NGHDQDLNHXRQFM-UHFFFAOYSA-N

物化性质

• 熔点：
  221-223 °C
• 沸点：
  465.0±45.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-氯苄基氨基)-3-氨基苯甲酸甲酯 在 sodium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 生成 3-Amino-4-(p-chlorophenylmethyl)aminobenzoic acid
  参考文献：
  名称：

  Synthesis of some new benzimidazolecarboxamides and evaluation of their antimicrobial activity

  摘要：

  A series of 1,2-disubstituted benzimidazole-5(6)-carboxamides was prepared and evaluated in vitro for antimicrobial activity against Staphyloccus aureus, Escherichia coli and Candida albicans. The precursor benzimidazolecarboxylic acids 4a-c and 9a-c were prepared via oxidative condensation of diaminobenzoic acids with aldehydes and via several steps over the 2(1H)-benzimidazolones, respectively. All acids were converted to their acyl chlorides with SOCI2, then amidified with several N,N'-dialkylaminoethyl derivatives. Compounds 8a-c, 20 and 22 exhibited the best activity. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00045-7
• 作为产物：
  描述：

  4-氯-3-硝基苯甲酸 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、275.79 kPa 条件下， 生成 4-(4-氯苄基氨基)-3-氨基苯甲酸甲酯
  参考文献：
  名称：

  某些带有酰胺或am基的新型1H-苯并咪唑-5-羧酸甲酯或乙酯的合成及强效抗菌活性。

  摘要：

  合成了一系列在C-2位带有酰胺或am取代的甲基或苯基基团的苯并咪唑-5-羧酸烷基酯衍生物，并评估了其对金黄色葡萄球菌，耐甲氧西林金黄色葡萄球菌（MRSA）的抗菌和抗真菌活性，粪链球菌，耐甲氧西林的表皮葡萄球菌（MRSE），大肠杆菌和白色念珠菌。结果表明，尽管所有简单的乙酰胺基本上都没有活性，但芳族酰胺和am具有强大的抗菌活性。芳族am衍生物13 fh对MRSA和MRSE表现出最佳的抑制活性，其1.56-0.39 microg / mL MIC值。

  DOI：

  10.1016/j.bmc.2004.12.025

文献信息

• Synthesis and Antioxidant Capacities of Some New Benzimidazole Derivatives
  作者：Gülgün Ayhan-Kılcıgil、Canan Kus、Elçin D. Özdamar、Benay Can-Eke、Mümtaz Iscan

  DOI：10.1002/ardp.200700088

  日期：2007.11

  In this study, we prepared some new oxadiazolyl benzimidazole derivatives and investigated their antioxidant properties by determination of microsomal NADPH‐dependent inhibition of lipid peroxidation levels (LP assay) and microsomal ethoxyresorufin O‐deethylase activity (EROD assay). Some of these compounds 20, 23 had slightly inhibitory effects (28%) on the lipid peroxidation levels at 10–3 M concentration

  在这项研究中，我们制备了一些新的恶二唑基苯并咪唑衍生物，并通过测定微粒体 NADPH 依赖性脂质过氧化水平抑制（LP 测定）和微粒体乙氧基试卤灵 O-脱乙基酶活性（EROD 测定）来研究它们的抗氧化性能。这些化合物 20、23 中的一些在低于标准 BHT (65%) 的 10-3 M 浓度下对脂质过氧化水平具有轻微的抑制作用 (28%)。5- [2- (Phenyl)-benzimidazol-1-yl-methyl]-2-mercapto-[1,3,4]-oxadiazole 16 被发现比咖啡因对乙氧基试卤灵 O-脱乙基酶的活性更强，IC50值 2.0 6 10-4 M。
• [EN] NOVEL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2009083526A1

  公开（公告）日：2009-07-09

  The invention relates to novel benzimidazole compounds of formula (I) wherein R1 to R1 are as defined in the specification, pharmaceutically acceptable salts thereof, to pharmaceutical compositions containing them and their use in medicine. In particular, the invention relates to compounds that are agonists of peroxisome proliferators-activated receptorγ (PPARγ).

  这项发明涉及公式（I）中R1到R1所定义的新型苯并咪唑化合物，其药学上可接受的盐，含有它们的药物组合物以及它们在医学上的用途。具体而言，该发明涉及激动过氧化物酶体增殖物激活受体γ（PPARγ）的激动剂化合物。
• Heterocyclic derivative and pharmaceutical composition comprising the same
  申请人：Kai Hiroyuki

  公开号：US09212130B2

  公开（公告）日：2015-12-15

  The present invention provides novel compounds having a P2X3 and/or P2X2/3 receptor antagonistic effect. A pharmaceutical composition having a P2X3 and/or P2X2/3 receptor antagonistic effect comprising a compound of the formula (I): wherein ring A is substituted or unsubstituted 5 to 7-membered cycloalkane, substituted or unsubstituted 5 to 7-membered cycloalkene or the like; C is a carbon atom; —X— is —N(R16)— or the like; R16 is hydrogen, substituted or unsubstituted alkyl or the like; R7 is substituted or unsubstituted 5- or 6-membered heteroaryl, substituted or unsubstituted 6 to 10 membered aryl; Q1 and Q2 are each independently a carbon atom or a nitrogen atom; -L- is —O—, —S— or the like; R6 is substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl or the like; R2 is hydrogen, hydroxy or the like, or its pharmaceutically acceptable salt or a solvate thereof.

  本发明提供了具有P2X3和/或P2X2/3受体拮抗作用的新化合物。具有P2X3和/或P2X2/3受体拮抗作用的药物组合物包括式(I)的化合物：其中环A是取代或未取代的5至7成员环烷烃，取代或未取代的5至7成员环烯烃等；C是碳原子；-X-是-N(R16)-等；R16是氢、取代或未取代的烷基等；R7是取代或未取代的5-或6-成员杂芳基，取代或未取代的6至10成员芳基；Q1和Q2分别是碳原子或氮原子；-L-是-O-、-S-等；R6是取代或未取代的环烷基，取代或未取代的环烯基等；R2是氢、羟基等，或其药学上可接受的盐或溶剂化合物。
• Discovery of GSK1997132B a novel centrally penetrant benzimidazole PPARγ partial agonist
  作者：Mairi Sime、Amanda C. Allan、Paul Chapman、Charlotte Fieldhouse、Gerard M.P. Giblin、Mark P. Healy、Millard H. Lambert、Lisa M. Leesnitzer、Ann Lewis、Raymond V. Merrihew、Richard A. Rutter、Rosemary Sasse、Barry G. Shearer、Timothy M. Wilson、Robert X. Xu、David J. Virley

  DOI：10.1016/j.bmcl.2011.06.088

  日期：2011.9

  The peroxisome proliferator-activated receptor gamma (PPAR gamma) is a ligand-activated nuclear receptor, thought to play a role in energy metabolism, glucose homeostasis and microglia-mediated neuroinflammation. A novel benzimidazole series of centrally penetrant PPAR gamma partial agonists has been identified. The optimization of PPAR gamma activity and in vivo pharmacokinetics leading to the identification of GSK1997132B a potent, metabolically stable and centrally penetrant PPAR gamma partial agonist, is described. (C) 2011 Elsevier Ltd. All rights reserved.
• NOVEL HETEROCYCLIC DERIVATIVES AND PHARMACEUTICAL COMPOSITION CONTAINING SAME
  申请人：Shionogi & Co., Ltd.

  公开号：EP2604260B1

  公开（公告）日：2017-05-10