methyl 3-amino-3-(m-tolyl)propanoate | 1038308-39-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 3-amino-3-(m-tolyl)propanoate
• 英文别名: methyl 3-amino-3-(3-methylphenyl)propanoate
• CAS: 1038308-39-2
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: CPKZXZUMMYNVHX-UHFFFAOYSA-N

物化性质

• 沸点：
  301.6±30.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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 3-amino-3-(m-tolyl)propanoate 在 水 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氯化碳 、 丙酮 为溶剂， 生成 3-benzamido-3-(3-methylphenyl)propanoic acid
  参考文献：
  名称：

  Synthesis, in Vitro and in Vivo Biological Evaluation, and Comprehensive Understanding of Structure−Activity Relationships of Dipeptidyl Boronic Acid Proteasome Inhibitors Constructed from β-Amino Acids

  摘要：

  An extensive structure-activity relationship (SAR) study of 72 dipeptidyl boronic acid proteasome inhibitors constructed from beta-amino acids is reported. SAR analysis revealed that bicyclic groups at the RI position, 3-F substituents at the R-2 position, and bulky aliphatic groups at the R-3 position were favorable to the activities. Enzymatic screening results showed that compound 78, comprising all of these features, was the most active inhibitor against the 20S human proteasome at less than a 2 nM level, as active as the marketed drug bortezomib. Cellular assays confirmed that compound 78 was the most potent against two hematologic and some solid tumor cells with IC50 values less than 1 mu M. Pharmacokinetic profiles suggested that 78 showed higher plasma exposure and a longer half-life than bortezomib.

  DOI：

  10.1021/jm1009742
• 作为产物：
  描述：

  3-甲基苯甲醛 在 氯化亚砜 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 methyl 3-amino-3-(m-tolyl)propanoate
  参考文献：
  名称：

  Synthesis and biological evaluation of 3-phenyl-3-aryl carboxamido propanoic acid derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26A1)

  摘要：

  All-trans-retinoic acid (ATRA), the biologically active metabolite of vitamin A, is used medicinally for the treatment of hyperproliferative diseases and cancers. However, it is easily metabolized. In this study, the leading compound S8 was found based on virtual screening. To improve the activity of the leading compound S8, a series of novel S8 derivatives were designed, synthesized and evaluated for their in vitro biological activities.All of the prepared compounds showed that substituting the 5-chloro-3-methyl-1-phenyl-1H-pyrazole group for the 2-tertbutyl-5-methylfuran scaffold led to a clear increase in the biological activity. The most promising compound 32, with a CYP26A1 IC50 value of 1.36 mu M (compared to liarozole (IC50 = 2.45 mu M) and S8 (IC50 = 3.21 mu M)) displayed strong inhibitory and differentiation activity against HL60 cells. In addition, the study focused on the effect of beta-phenylalanine, which forms the coordination bond with the heme of CYP26A1. These studies suggest that the compound 32 can be used as an appropriate candidate for future development. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.036

文献信息

• Heterodimers of glutamic acid
  申请人：Molecular Insight Pharmaceuticals, Inc.

  公开号：US10640461B2

  公开（公告）日：2020-05-05

  Compounds of Formula (Ia) wherein R is a C6-C12 substituted or unsubstituted aryl, a C6-C12 substituted or unsubstituted heteroaryl, a C1-C6 substituted or unsubstituted alkyl or —NR′R′, Q is C(O), O, NR′, S, S(O)2, C(O)2 (CH2)p Y is C(O), O, NR′, S, S(O)2, C(O)2 (CH2)p Z is H or C1-C4 alkyl, R′ is H, C(O), S(O)2, C(O)2, a C6-C12 substituted or unsubstituted aryl, a C6-C12 substituted or unsubstituted heteroaryl or a C1-C6 substituted or unsubstituted alkyl, when substituted, aryl, heteroaryl and alkyl are substituted with halogen, C6-C12 heteroaryl, —NR′R′ or COOZ, which have diagnostic and therapeutic properties, such as the treatment and management of prostate cancer and other diseases related to NAALADase inhibition. Radiolabels can be incorporated into the structure through a variety of prosthetic groups attached at the X amino acid side chain via a carbon or hetero atom linkage.

  式（Ia）化合物 其中 R 是 C6-C12 取代或未取代的芳基、C6-C12 取代或未取代的杂芳基、C1-C6 取代或未取代的烷基或 -NR′R′、 Q 是 C(O)、O、NR′、S、S(O)2、C(O)2 (CH2)p Y 是 C(O)、O、NR′、S、S(O)2、C(O)2 (CH2)p Z 是 H 或 C1-C4 烷基、 R′ 是 H、C(O)、S(O)2、C(O)2、取代或未取代的 C6-C12 芳基、取代或未取代的 C6-C12 杂芳基或取代或未取代的 C1-C6 烷基，当芳基、杂芳基和烷基被卤素取代时、C6-C12杂芳基、-NR′R′或 COOZ，它们具有诊断和治疗特性，如治疗和控制前列腺癌以及与 NAALADase 抑制有关的其他疾病。放射性标记可通过碳原子或杂原子连接在 X 氨基酸侧链上的各种人工基团掺入结构中。
• Azetidin-2-one-based small molecules as dual hHDAC6/HDAC8 inhibitors: Investigation of their mechanism of action and impact of dual inhibition profile on cell viability
  作者：Stefano Federico、Tuhina Khan、Anna Fontana、Simone Brogi、Rosaria Benedetti、Federica Sarno、Gabriele Carullo、Alex Pezzotta、Akella Prasanth Saraswati、Eugenia Passaro、Luca Pozzetti、Alessandro Papa、Nicola Relitti、Sandra Gemma、Stefania Butini、Anna Pistocchi、Anna Ramunno、Fabrizio Vincenzi、Katia Varani、Vanessa Tatangelo、Laura Patrussi、Cosima T. Baldari、Simona Saponara、Beatrice Gorelli、Stefania Lamponi、Massimo Valoti、Fulvio Saccoccia、Marialaura Giannaccari、Giovina Ruberti、Daniel Herp、Manfred Jung、Lucia Altucci、Giuseppe Campiani

  DOI：10.1016/j.ejmech.2022.114409

  日期：2022.8
• HETERODIMERS OF GLUTAMIC ACID
  申请人：Molecular Insight Pharmaceuticals, Inc.

  公开号：EP2942065B1

  公开（公告）日：2018-06-27
• Heterodimers of Glutamic Acid
  申请人：Molecular Insight Pharmaceuticals, Inc.

  公开号：US20170044098A1

  公开（公告）日：2017-02-16

  Compounds of Formula (Ia) wherein R is a C 6 -C 12 substituted or unsubstituted aryl, a C 6 -C 12 substituted or unsubstituted heteroaryl, a C 1 -C 6 substituted or unsubstituted alkyl or —NR′R′, Q is C(O), O, NR′, S, S(O) 2 , C(O) 2 (CH 2 )p Y is C(O), O, NR′S, S(O) 2 , C(O) 2 (CH 2 )p Z is H or C 1- C 4 alkyl, R′ is H, C(O), S(O) 2 , C(O) 2 , a C 6 -C 12 substituted or unsubstituted aryl, a C 6 -C 12 substituted or unsubstituted heteroaryl or a C 1 -C 6 substituted or unsubstituted alkyl, when substituted, aryl, heteroaryl and alkyl are substituted with halogen, C 6 -C 12 heteroaryl, —NR′R′ or COOZ, which have diagnostic and therapeutic properties, such as the treatment and management of prostate cancer and other diseases related to NAALADase inhibition, Radiolabels can be incorporated into the structure through a variety of prosthetic groups attached at the X amino acid side chain via a carbon or hetero atom linkage.
• US9878980B2
  申请人：——

  公开号：US9878980B2

  公开（公告）日：2018-01-30