3-(4-(methoxycarbonyl)phenyl)-2-methylpropanoic acid | 122594-17-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(4-(methoxycarbonyl)phenyl)-2-methylpropanoic acid
• 英文别名: 3-[4-(Methoxycarbonyl)phenyl]-2-methylpropanoic acid；3-(4-methoxycarbonylphenyl)-2-methylpropanoic acid
• CAS: 122594-17-6
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: KLSUVGBPKPQQPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-(methoxycarbonyl)phenyl)-2-methylpropanoic acid 在 钯 2,4,6-三甲基吡啶 、 盐酸 、 sodium hydroxide 、 氯化亚砜 、 sodium azide 、 氢气 、 双氧水 、 sodium methylate 、 溶剂黄146 、 三乙胺 、 锌 、 氯甲酸异丁酯 作用下， 以 甲醇 、 乙醇 、 乙二醇甲醚 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 125.0h， 生成 9-methyl-10-deazaminopterin diethyl ester
  参考文献：
  名称：

  Synthesis and antifolate properties of 9-alkyl-10-deazaminopterins

  摘要：

  Reformatski condensation of benzyl 2-bromopropionate with 4-carbomethoxybenzaldehyde, followed by dehydration afforded benzyl 2-methyl-p-carbomethoxycinnamate (4a). Hydrogenation over a Pd catalyst gave the hydrocinnamic acid 5a. Conversion to the chloromethyl (6a) and azidomethyl ketone (7a) was followed by hydrogenation to the aminomethyl ketone (8a). Direct N-alkylation by 2,4-diamino-5-nitro-6-chloropyrimidine followed by reductive ring closure in Zn-HOAc and subsequent saponification of the benzoate ester yielded 4-amino-4-deoxy-9-methyl-10-deazapteroic acid (11a). Coupling with diethyl L-glutamate and saponification afforded 9-methyl-10-deazaminopterin (13a). The 9-ethyl analogue (13b) was similarly prepared from benzyl 2-bromobutyrate. The 9-methyl analogue (13a) was 21 times more potent than MTX as an inhibitor of cell growth in L1210 cells. The reason for this enhanced cytotoxicity in L1210 is unclear, since enzyme inhibition and transport parameters were similar to those of MTX. In human Manca leukemia cells growth inhibition was not dramatic and paralleled MTX.

  DOI：

  10.1021/jm00163a035
• 作为产物：
  描述：

  methyl 4-[(E)-2-methyl-3-oxo-3-phenylmethoxyprop-1-enyl]benzoate 生成 3-(4-(methoxycarbonyl)phenyl)-2-methylpropanoic acid
  参考文献：
  名称：

  DEGRAW, JOSEPH I.;CHRISTIE, PAMELA H.;KISLIUK, ROY L.;GAUMONT, YVETTE;SIR+, J. MED. CHEM., 33,(1990) N, C. 212-215

  摘要：

  DOI：

文献信息

• Aryl cyclopropyl-amino-isoquinolinyl amide compounds
  申请人：Aerie Pharmaceuticals, Inc.

  公开号：US10858339B2

  公开（公告）日：2020-12-08

  Provided herein are arylcyclopropyl amino-isoquinoline amide compounds. In particular, the disclosure provides compounds that affect the function of kinases in a cell and that are useful as therapeutic agents or with therapeutic agents. The compounds of the disclosure are useful in the treatment of a variety of diseases and conditions including eye diseases such as glaucoma, cardiovascular diseases, diseases characterized by abnormal growth, such as cancers, and inflammatory diseases. The disclosure further provides compositions containing isoquinoline amide compounds.

  本文提供的是芳基环丙基氨基异喹啉酰胺化合物。特别是，本公开提供的化合物可影响细胞中激酶的功能，并可作为治疗剂或与治疗剂一起使用。本公开的化合物可用于治疗多种疾病和病症，包括眼部疾病（如青光眼）、心血管疾病、以异常生长为特征的疾病（如癌症）以及炎症性疾病。本公开进一步提供了含有异喹啉酰胺化合物的组合物。
• Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals
  作者：Fu-Peng Wu、Da Li、Jin-Bao Peng、Xiao-Feng Wu

  DOI：10.1021/acs.orglett.9b02047

  日期：2019.7.19

  In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.
• DEGRAW, JOSEPH I.;CHRISTIE, PAMELA H.;KISLIUK, ROY L.;GAUMONT, YVETTE;SIR+, J. MED. CHEM., 33,(1990) N, C. 212-215
  作者：DEGRAW, JOSEPH I.、CHRISTIE, PAMELA H.、KISLIUK, ROY L.、GAUMONT, YVETTE、SIR+

  DOI：——

  日期：——
• MPAI-Ligand Accelerated Pd-Catalyzed C(<i>sp</i>³)–H Arylation of Free Aliphatic Acids
  作者：Zi-Yu Dong、Jia-Hui Zhao、Peng Wang、Jin-Quan Yu

  DOI：10.1021/acs.orglett.2c02933

  日期：2022.10.28
• ARYL CYCLOPROPYL-AMINO-ISOQUINOLINYL AMIDE COMPOUNDS
  申请人：Aerie Pharmaceuticals, Inc.

  公开号：US20210002253A1

  公开（公告）日：2021-01-07

  Provided herein are arylcyclopropyl amino-isoquinoline amide compounds. In particular, the disclosure provides compounds that affect the function of kinases in a cell and that are useful as therapeutic agents or with therapeutic agents. The compounds of the disclosure are useful in the treatment of a variety of diseases and conditions including eye diseases such as glaucoma, cardiovascular diseases, diseases characterized by abnormal growth, such as cancers, and inflammatory diseases. The disclosure further provides compositions containing isoquinoline amide compounds.