(±)-methyl 2-(4-amino-3-chlorophenyl)propanoate | 67333-29-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (±)-methyl 2-(4-amino-3-chlorophenyl)propanoate
• 英文别名: methyl 2-(4-amino-3-chlorophenyl)propanoate；methyl 2-(4-amino-3-chlorophenyl)propionate；methyl α-(3-chloro-4-aminophenyl)propionate；Methyl alpha-(3-chloro-4-aminophenyl)propionate
• CAS: 67333-29-3
• 化学式: C₁₀H₁₂ClNO₂
• 分子量: 213.664
• InChiKey: FIXQKXUNWRZJSA-UHFFFAOYSA-N

物化性质

• 沸点：
  168-172 °C(Press: 1 Torr)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (±)-methyl 2-(4-amino-3-chlorophenyl)propanoate 在 盐酸 、 4-二甲氨基吡啶 、 水 、 palladium diacetate 、 potassium carbonate 、 sodium nitrite 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙二醇甲醚 、 水 、 乙腈 为溶剂， 反应 78.0h， 生成 (±)-2-[3-chloro-4-[3-(hexylcarbamoyloxy)phenyl]phenyl]propanoic acid
  参考文献：
  名称：

  Potent multitarget FAAH-COX inhibitors: Design and structure-activity relationship studies

  摘要：

  Non-steroidal anti-inflammatory drugs (NSAIDs) exert their pharmacological effects by inhibiting cyclooxygenase (COX)-1 and COX-2. Though widely prescribed for pain and inflammation, these agents have limited utility in chronic diseases due to serious mechanism-based adverse events such as gastrointestinal damage. Concomitant blockade of fatty acid amide hydrolase (FAAH) enhances the therapeutic effects of the NSAIDs while attenuating their propensity to cause gastrointestinal injury. This favorable interaction is attributed to the accumulation of protective FAAH substrates, such as the endocannabinoid anandamide, and suggests that agents simultaneously targeting COX and FAAH might provide an innovative strategy to combat pain and inflammation with reduced side effects. Here, we describe the rational design and structure-active relationship (SAR) properties of the first class of potent multitarget FAAH-COX inhibitors. A focused SAR exploration around the prototype 10r (ARN2508) led to the identification of achiral (18b) as well as racemic (29a-c and 29e) analogs. Absolute configurational assignment and pharmacological evaluation of single enantiomers of 10r are also presented. (S)-(+)-10r is the first highly potent and selective chiral inhibitor of FAAH-COX with marked in vivo activity, and represents a promising lead to discover novel analgesics and anti-inflammatory drugs. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.036
• 作为产物：
  描述：

  (±)-2-(3-chloro-4-nitrophenyl)propanoic acid 在 palladium on activated charcoal 硫酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 (±)-methyl 2-(4-amino-3-chlorophenyl)propanoate
  参考文献：
  名称：

  非甾体抗炎药。2。[（杂芳基氨基）苯基]链烷酸。

  摘要：

  制备了具有吡啶，喹啉或嘧啶作为杂芳基部分的一系列[（杂芳基氨基）苯基]链烷酸作为潜在的抗炎剂。其中，2- [4-（2-吡啶基氨基）苯基]丙酸（14b）具有出色的抗炎和镇痛活性，较少引起胃副反应。讨论了构效关系。

  DOI：

  10.1021/jm00356a019

文献信息

• Novel .alpha.-thio-alkanoic acid derivatives
  申请人：Sagami Chemical Research Center

  公开号：US04242519A1

  公开（公告）日：1980-12-30

  Novel .alpha.-thio-alkanoic acid derivatives and a process for their preparation. These novel compounds can be easily converted to useful medicines.

  新颖的α-硫代烷酸衍生物及其制备方法。这些新颖化合物可以轻松转化为有用的药物。
• 1,2 Dihydro- and 1,2,3,4-tetrahydro quinolylacetic acids and analgesic
  申请人：Nippon Zoki Pharmaceutical Co.

  公开号：US04555513A1

  公开（公告）日：1985-11-26

  Novel quinolylacetic acid compounds of the formula (I): ##STR1## wherein R.sub.1 is a member selected from the group consisting of hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, and a lower alkyl group having 1 to 4 carbon atoms substituted with an aromatic group having a substituent; R.sub.2 is a member selected from the group consisting of hydrogen atom and a lower alkyl group having 1 to 4 carbon atoms; R.sub.3 is a member selected from the group consisting of hydrogen, a halogen atom, an alkyl group having 1 to 8 carbon atoms, and an alkenyl group having 2 to 8 carbon atoms; R.sub.4 and R.sub.5, carpable of cyclization, are each a member selected from the group consisting of hydrogen atom and a lower alkyl group having 1 to 4 carbon atoms; R.sub.6 is a member selected from the group consisting of hydrogen atom an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an alkynyl group having 3 to 8 carbon atoms, an aralkyl group, a substituted aralkyl group, an aliphatic or aromatic acyl group, and a substituted aliphatic or aromatic acyl group; and A is a member selected from the group consisting of hydrogen atom and an oxo group; the broken line denoting a second bond or no bond when A is a hydrogen atom and denoting no bond when A is an oxo group, and pharmaceutically acceptable salts thereof.

  化合物的结构式 (I)：##STR1## 其中 R.sub.1 是从氢原子、具有 1 到 4 个碳原子的较低烷基基团，以及具有取代基的芳基的 1 到 4 个碳原子的较低烷基基团中选择的成员；R.sub.2 是从氢原子和具有 1 到 4 个碳原子的较低烷基基团中选择的成员；R.sub.3 是从氢、卤素原子、具有 1 到 8 个碳原子的烷基基团和具有 2 到 8 个碳原子的烯基基团中选择的成员；R.sub.4 和 R.sub.5，可进行环化，分别是从氢原子和具有 1 到 4 个碳原子的较低烷基基团中选择的成员；R.sub.6 是从氢原子、具有 1 到 8 个碳原子的烷基基团、具有 2 到 5 个碳原子的烯基基团、具有 3 到 8 个碳原子的炔基基团、芳基烷基基团、取代芳基烷基基团、脂肪或芳香族酰基团以及取代脂肪或芳香族酰基团中选择的成员；A 是从氢原子和氧代基中选择的成员；断线表示第二键或当 A 是氢原子时无键，并且当 A 是氧代基时表示无键，以及其药用盐。
• .alpha.-Methylthio-.alpha.-(p-phthalimidophenyl)-propionic acid
  申请人：Sagami Chemical Research Center

  公开号：US04308208A1

  公开（公告）日：1981-12-29

  The present invention provides .alpha.-methylthio-.alpha.-(p-phthalimidophenyl)-propionic acid and its esters of the formula: ##STR1## wherein R' represents H or C.sub.1 -C.sub.4 alkyl. The subject compounds are useful as intermediates e.g. for Indoprofen.

  本发明提供了α-甲基硫代-α-(p-邻苯二甲酰亚氨基苯基)-丙酸及其酯的化学式：##STR1## 其中R'代表H或C.sub.1-C.sub.4烷基。该化合物可用作中间体，例如用于制备印托芬。
• New quinolylacetic acid compounds and pharmaceutical compositions containing them
  申请人：NIPPON ZOKI PHARMACEUTICAL CO. LTD.

  公开号：EP0083222A1

  公开（公告）日：1983-07-06

  Novel quinolylacetic acid compounds have the general formula in which R, is a hydrogen atom or an esterifying group, e.g. a lower alkyl group which may optionally be substituted with an aromatic group that is itself optionally substituted, R2 is a hydrogen atom or a lower alkyl group, R3 is a hydrogen or halogen atom or an alkyl or alkenyl group, each of R4 and R5, which are the same as or different from one another, is a hydrogen atom or a lower alkyl group, or R4 and R5 are joined to form a ring with the carbon atom they are both attached to, R6 is a hydrogen atom or an alkyl, alkenyl, alkynyl, aralkyl or acyl group which may optionally be substituted and A is a hydrogen atom or an oxo group, the broken line representing optional unsaturation when A is a hydrogen atom or are pharmaceutically acceptable salts of such compounds. Such compounds and salts have antipyretic, analgesic and antiinflammantory actions and are less toxic than known drugs having similar uses. They are made up with pharmaceutical compositions for administration to patients.

  新型喹啉乙酸化合物的通式为 其中 R 是氢原子或酯化基团，例如R2 是氢原子或低级烷基，R3 是氢原子或卤素原子或烷基或烯基，R4 和 R5（彼此相同或不同）各自是氢原子或低级烷基、R6是氢原子或烷基、烯基、炔基、芳基或酰基，可任选被取代，A是氢原子或氧代基团，当A是氢原子时，断线代表任选的不饱和度，或者是此类化合物的药学上可接受的盐。 此类化合物和盐具有解热、镇痛和消炎作用，毒性低于具有类似用途的已知药物。这些化合物和盐可制成药剂组合物，供患者使用。
• [EN] CDK2 INHIBITOR AND PREPARATION METHOD THEREFOR<br/>[FR] INHIBITEUR DE CDK2 ET SON PROCÉDÉ DE PRÉPARATION<br/>[ZH] CDK2抑制剂及其制备方法
  申请人：[en]TUOJIE BIOTECH (SHANGHAI) CO., LTD.;[zh]上海拓界生物医药科技有限公司

  公开号：WO2022135442A1

  公开（公告）日：2022-06-30

  本公开提供了CDK2抑制剂及其制备方法。具体而言，本公开提供一种式I所示化合物或其可药用的盐、互变异构体，其中各基团如本公开定义。所述式I所示化合物可作为细胞周期蛋白-依赖性激酶抑制剂，用于预防和/或治疗与蛋白依赖性激酶或细胞周期蛋白相关的疾病，例如细胞增殖性疾病，癌症或免疫性疾病。