methyl 4-(3-aminophenethyl)benzoate | 872450-76-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl 4-(3-aminophenethyl)benzoate
• 英文别名: methyl 4-[2-(3-aminophenyl)ethyl]benzoate
• CAS: 872450-76-5
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: SHKPOPQTWCFCDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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 4-(3-aminophenethyl)benzoate 在 吡啶 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(2-aminophenyl)-4-(3-((4-methoxyphenyl)sulfonamido)phenethyl)benzamide
  参考文献：
  名称：

  Design, synthesis, and evaluation of N-phenyl-4-(2-phenylsulfonamido)-benzamides as microtubule-targeting agents in drug-resistant cancer cells, displaying HDAC inhibitory response

  摘要：

  Microtubule-targeting agents (MTA) have enjoyed significant clinical success for decades. However, several mechanisms may cause inactivation of such drugs, leading to acquired resistance in patients treated with them. Therefore, drugs containing a stilbene-like skeleton and possessing dual inhibitory activity may provide a new and differentiated treatment for patients to overcome challenging acquired resistance. A new compound (16c) displays promising anticancer activity with GI(50) of 22 +/- 2 and 12 +/- 0.1 nM in vincristine-resistant nasopharyngeal (KB-Vin) cancer cells and etoposide-resistant nasopharyngeal (KB-7D) cancer cells and is better than vincristine, etoposide, ABT-751, and MS-275. A mechanistic study revealed that 16c interferes with the cell cycle distribution and induces cell cycle arrest at the G2/M phase and severe mitotic spindle defects followed by apoptosis. In addition, it produces much more significant cytotoxicity than vincristine and etoposide in the corresponding resistant cells, indicating that it may be a promising candidate to overcome drug resistance in cancer cells. Compound 16c also displays inhibitory activity against HDAC 1 and HDAC 2 with IC50 values of 1.07 mu M, and 1.47 mu M, respectively. These findings may lead to a new type of structural motif for future development of drugs that could overcome acquired resistance to MTAs. (c) 2020 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2020.112158
• 作为产物：
  描述：

  (4-甲氧羰基苄基)三苯基溴化膦 在 palladium 10% on activated carbon 、 氢气 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 methyl 4-(3-aminophenethyl)benzoate
  参考文献：
  名称：

  Design, synthesis, and evaluation of N-phenyl-4-(2-phenylsulfonamido)-benzamides as microtubule-targeting agents in drug-resistant cancer cells, displaying HDAC inhibitory response

  摘要：

  Microtubule-targeting agents (MTA) have enjoyed significant clinical success for decades. However, several mechanisms may cause inactivation of such drugs, leading to acquired resistance in patients treated with them. Therefore, drugs containing a stilbene-like skeleton and possessing dual inhibitory activity may provide a new and differentiated treatment for patients to overcome challenging acquired resistance. A new compound (16c) displays promising anticancer activity with GI(50) of 22 +/- 2 and 12 +/- 0.1 nM in vincristine-resistant nasopharyngeal (KB-Vin) cancer cells and etoposide-resistant nasopharyngeal (KB-7D) cancer cells and is better than vincristine, etoposide, ABT-751, and MS-275. A mechanistic study revealed that 16c interferes with the cell cycle distribution and induces cell cycle arrest at the G2/M phase and severe mitotic spindle defects followed by apoptosis. In addition, it produces much more significant cytotoxicity than vincristine and etoposide in the corresponding resistant cells, indicating that it may be a promising candidate to overcome drug resistance in cancer cells. Compound 16c also displays inhibitory activity against HDAC 1 and HDAC 2 with IC50 values of 1.07 mu M, and 1.47 mu M, respectively. These findings may lead to a new type of structural motif for future development of drugs that could overcome acquired resistance to MTAs. (c) 2020 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2020.112158

文献信息

• [EN] PHENYLCARBOXYLIC ACID DERIVATIVES AND USE THEREOF FOR THE TREATMENT OF DIABETES<br/>[FR] DERIVES D'ACIDE PHENYLCARBOXYLIQUE, ET LEUR UTILISATION POUR TRAITER LE DIABETE
  申请人：MERCK PATENT GMBH

  公开号：WO2006000288A1

  公开（公告）日：2006-01-05

  The invention relates to compounds of general formula (1): in which R1, R2, R3, R4, R5, A, B, D and E are as defined in Claim 1, and also to the preparation process therefor and the therapeutic use thereof. These compounds can be used in the treatment of pathologies associated with hyperglycaemia.

  该发明涉及一般式（1）的化合物：其中R1、R2、R3、R4、R5、A、B、D和E如权利要求1所定义，并且还涉及其制备过程和治疗用途。这些化合物可用于治疗与高血糖相关的病理。
• DICARBOXYLIC ACID COMPOUND
  申请人：DAIICHI SANKYO COMPANY, LIMITED

  公开号：US20160046568A1

  公开（公告）日：2016-02-18

  It is an object of the present invention to provide a medicament for preventing or treating hyperphosphatemia. Solution: A compound represented by a general formula (I) or a pharmacologically acceptable salt thereof. [In the formula, R 1 : a methyl group or the like, R 2 : a hydrogen atom or the like, R 3 : a hydrogen atom or the like, A: a cyclohexyl ring or the like, X: CH or the like, Y: CH or the like, Z: CH or the like, and n: 2 or the like.]

  本发明的目的是提供一种用于预防或治疗高磷血症的药物。解决方案：由通式（I）表示的化合物或其药理学可接受的盐。【在公式中，R1：甲基基团或类似物，R2：氢原子或类似物，R3：氢原子或类似物，A：环己基环或类似物，X：CH或类似物，Y：CH或类似物，Z：CH或类似物，n：2或类似物。】
• Phenylcarboxylic Acid Derivatives and Use Thereof for the Treatment of Diabetes
  申请人：Moinet Gerard

  公开号：US20080045483A1

  公开（公告）日：2008-02-21

  The invention relates to compounds of general formula (1): in which R1, R2, R3, R4, R5, A, B, D and E are as defined in Claim 1 , and also to the preparation process therefor and the therapeutic use thereof. These compounds can be used in the treatment of pathologies associated with hyperglycaemia.

  本发明涉及一般式（1）的化合物：其中R1、R2、R3、R4、R5、A、B、D和E如权利要求书所定义，并且涉及其制备过程和治疗用途。这些化合物可用于治疗与高血糖相关的病理状况。
• AMINOALKYL-SUBSTITUTED N-THIENYLBENZAMIDE DERIVATIVE
  申请人：ASTELLAS PHARMA INC.

  公开号：US20150031727A1

  公开（公告）日：2015-01-29

  [Problem] To provide a compound that has an intestinal phosphate transporter (NPT-IIb) inhibitory action and is useful as an active ingredient of an agent for treating and/or preventing hyperphosphatemia. [Means for Solution] The present inventors conducted their studies on a compound that has an NPT-IIb inhibitory action and is useful as an active ingredient of an agent for treating and/or preventing hyperphosphatemia. As a result, they created an aminoalkyl-substituted N-thienylbenzamide derivative which has NPT-IIb inhibitory action, thereby completing the present invention. The aminoalkyl-substituted N-thienylbenzamide derivative of the present invention has an NPT-IIb inhibitory action and can be used as an agent for preventing and/or treating hyperphosphatemia.

  【问题】提供一种具有肠道磷酸转运体（NPT-IIb）抑制作用并且可用作治疗和/或预防高磷血症药物的活性成分的化合物。【解决方案】本发明人对一种具有NPT-IIb抑制作用并且可用作治疗和/或预防高磷血症药物的活性成分的化合物进行了研究。结果，他们创造了一种具有NPT-IIb抑制作用的氨基烷基取代的N-噻吩基苯酰胺衍生物，从而完成了本发明。本发明的氨基烷基取代的N-噻吩基苯酰胺衍生物具有NPT-IIb抑制作用，并可用作预防和/或治疗高磷血症的药物。
• AMINOALKYL-SUBSTITUTED N-THIENYL BENZAMIDE DERIVATIVE
  申请人：Astellas Pharma Inc.

  公开号：EP2772490B1

  公开（公告）日：2016-04-06