3-氨基-3-(2-甲基苯基)丙酸甲酯 | 1009692-04-9

• 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
• 中文名称: 3-氨基-3-(2-甲基苯基)丙酸甲酯
• 英文名称: 3-amino-3-o-tolyl-propionic acid methyl ester
• 英文别名: methyl 3-amino-3-(2-methylphenyl)propanoate
• CAS: 1009692-04-9
• 化学式: C₁₁H₁₅NO₂
• mdl: MFCD11200708
• 分子量: 193.246
• InChiKey: OIKMAUPHKQQGOX-UHFFFAOYSA-N

物化性质

• 沸点：
  302.7±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：
  0.363
• 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：

  3-氨基-3-(2-甲基苯基)丙酸甲酯 在 盐酸 、 异丁基硼酸 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 四氯化碳 、 正己烷 、 二氯甲烷 、 水 、 丙酮 为溶剂， 生成 (R)-1-[3-benzamido-3-(2-methylphenyl)propanamido]-3-methylbutylboronic 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：

  2-甲基苯甲醛 在 氯化亚砜 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 36.0h， 生成 3-氨基-3-(2-甲基苯基)丙酸甲酯
  参考文献：
  名称：

  Construction of β‐Phenylalanine Derivatives through Pd‐Catalyzed, C(sp²)−H (ortho) Functionalization

  摘要：

  摘要 本文介绍了钯(II)催化、吡啶酰胺定向基团辅助的外消旋和对映纯 β-苯丙氨酸和 3-氨基-3-苯基丙醇（1,3-氨基醇）的 C(sp2)-H（正交）官能化。尝试了 C(sp2)-H（正交）官能化，包括芳基化、溴化、碘化和烷氧基化。通过 C(sp2)-H（正交）芳基化反应得到了双芳基或三联苯型 β-苯丙氨酸支架，通过卤化和甲氧基化反应得到了正交 C-H 卤化或甲氧基化 β-苯丙氨酸。此外，还研究了含有 C（sp2）-H 键和远端 C（sp3）-H 键的正交甲基取代的 β-苯丙氨酸的 C-H 芳基化反应。β -苯丙氨酸是一种芳基化的 β -氨基酸基团，存在于各种天然产物、生物活性分子和 β -肽中，是具有药用活性的化合物的前体。因此，这项工作有助于通过位点选择性 C-H 功能化来扩展非天然 β-苯丙氨酸（β-氨基酸）衍生物库。

  DOI：

  10.1002/ejoc.202300463

文献信息

• SUBSTITUTED 3-THIAZOLOAMINO-PROPIONIC ACID DERIVATIVES AND THEIR USE AS PHARMACEUTICALS
  申请人：RUF Sven

  公开号：US20130053402A1

  公开（公告）日：2013-02-28

  The present invention relates to compounds of the formulae Ia and Ib, wherein G, R 10 , R 30 , R 40 , R 50 and R 60 have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. They are inhibitors of the protease cathepsin A, and are useful for the treatment of diseases such as atherosclerosis, heart failure, renal diseases, liver diseases or inflammatory diseases, for example. The invention furthermore relates to processes for the preparation of the compounds of the formulae Ia and Ib, their use and pharmaceutical compositions comprising them.

  本发明涉及式Ia和式Ib的化合物，其中G、R10、R30、R40、R50和R60具有索赔中指示的含义，它们是有价值的药用活性化合物。它们是蛋白酶卡特普辛A的抑制剂，用于治疗动脉粥样硬化、心力衰竭、肾脏疾病、肝脏疾病或炎症性疾病等疾病。此外，该发明还涉及制备式Ia和式Ib化合物的方法，它们的用途以及包含它们的药物组合物。
• [EN] SUBSTITUTED 3 - (THIAZOLE - 4 - CARBONYL) - OR 3 - (THIAZOLE - 2 - CARBONYL) AMINOPROPIONIC ACID DERIVATIVES AND THEIR USE AS PHARMACEUTICALS<br/>[FR] DÉRIVÉS D'ACIDE 3-(THIAZOLE-4-CARBONYL)AMINOPROPIONIQUE OU 3-(THIAZOLE-2-CARBONYL)AMINOPROPIONIQUE SUBSTITUÉ ET LEUR UTILISATION COMME PRODUITS PHARMACEUTIQUES
  申请人：SANOFI SA

  公开号：WO2013014205A1

  公开（公告）日：2013-01-31

  The present invention relates to compounds of the formulae (Ia) and (Ib), wherein G, R10, R30, R40, R50 and R60 have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. They are inhibitors of the protease cathepsin A, and are useful for the treatment of diseases such as atherosclerosis, heart failure, renal diseases, liver diseases or inflammatory diseases, for example. The invention furthermore relates to processes for the preparation of the compounds of the formulae la and lb, their use and pharmaceutical compositions comprising them.

  本发明涉及具有式(Ia)和(Ib)的化合物，其中G、R10、R30、R40、R50和R60具有索引的含义，这些化合物是有价值的药用活性化合物。它们是蛋白酶卡特普辛A的抑制剂，可用于治疗动脉粥样硬化、心力衰竭、肾脏疾病、肝脏疾病或炎症性疾病等疾病。此外，该发明还涉及制备式Ia和Ib化合物的方法，它们的用途以及包含它们的药物组成物。
• 3-HETEROAROYLAMINO-PROPIONIC ACID DERIVATIVES AND THEIR USE AS PHARMACEUTICALS
  申请人：RUF Sven

  公开号：US20130053416A1

  公开（公告）日：2013-02-28

  3-Heteroaroylamino-propionic acid derivatives and their use as pharmaceuticals The present invention relates to compounds of the formula I, wherein Ht, G, R 10 , R 30 , R 40 , R 50 and R 60 have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. They are inhibitors of the protease cathepsin A, and are useful for the treatment of diseases such as atherosclerosis, heart failure, renal diseases, liver diseases or inflammatory diseases, for example. The invention furthermore relates to processes for the preparation of the compounds of the formula I, their use and pharmaceutical compositions comprising them.

  3-杂环酰氨基丙酸衍生物及其作为药物的用途。本发明涉及具有以下式I的化合物，其中Ht，G，R10，R30，R40，R50和R60具有权利要求中所示的含义，这些化合物是有价值的药用活性化合物。它们是蛋白酶卡特普辛A的抑制剂，可用于治疗动脉粥样硬化、心力衰竭、肾脏疾病、肝脏疾病或炎症性疾病等疾病。此外，本发明还涉及制备具有式I的化合物的方法，它们的用途以及包含它们的药物组合物。
• Substituted 3-thiazoloamino-propionic acid derivatives and their use as pharmaceuticals
  申请人：Ruf Sven

  公开号：US09174952B2

  公开（公告）日：2015-11-03

  The present invention relates to compounds of the formulae Ia and Ib, wherein G, R10, R30, R40, R50 and R60 have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. They are inhibitors of the protease cathepsin A, and are useful for the treatment of diseases such as atherosclerosis, heart failure, renal diseases, liver diseases or inflammatory diseases, for example. The invention furthermore relates to processes for the preparation of the compounds of the formulae Ia and Ib, their use and pharmaceutical compositions comprising them.

  本发明涉及式Ia和式Ib的化合物，其中G、R10、R30、R40、R50和R60具有所述权利要求中所示的含义，它们是有价值的药物活性化合物。它们是蛋白酶卡特普西A的抑制剂，可用于治疗动脉粥样硬化、心力衰竭、肾脏疾病、肝脏疾病或炎症性疾病等疾病。本发明还涉及制备式Ia和式Ib化合物的过程、它们的用途以及包含它们的制药组合物。
• [EN] 3-HETEROAROYLAMINO-PROPIONIC ACID DERIVATIVES AND THEIR USE AS PHARMACEUTICALS<br/>[FR] DÉRIVÉS D'ACIDE 3-HÉTÉROAROYLAMINOPROPIONIQUE ET LEUR UTILISATION COMME PRODUITS PHARMACEUTIQUES
  申请人：SANOFI SA

  公开号：WO2013014204A3

  公开（公告）日：2013-04-04