methyl 2-(3-chloropropanamido)benzoate | 37795-76-9

• 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-(3-chloropropanamido)benzoate
• 英文别名: Methyl-o-(β-chlorpropionamid)-benzoat；2-(3-Chlorpropionamido)benzoesaeuremethylester；Methyl-o-(α-chlorpropionamid)-benzoat；2-(3-chloro-propionylamino)-benzoic acid methyl ester；Methyl 2-[(3-chloropropanoyl)amino]benzoate；methyl 2-(3-chloropropanoylamino)benzoate
• CAS: 37795-76-9
• 化学式: C₁₁H₁₂ClNO₃
• mdl: MFCD00121724
• 分子量: 241.674
• InChiKey: OWAOXUCRJSRPHS-UHFFFAOYSA-N

物化性质

• 熔点：
  94 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-chloropropanamido)benzoate 在 羟胺 作用下， 以 乙醇 为溶剂， 生成 2,3-二氢-[1,2]恶唑并[3,2-b]喹唑啉-9-酮
  参考文献：
  名称：

  Reisner; Ludwig; Simon, Arzneimittel-Forschung/Drug Research, 1977, vol. 27, # 4, p. 766 - 770

  摘要：

  DOI：
• 作为产物：
  描述：

  邻氨基苯甲酸甲酯 、 3-氯丙酰氯 在 吡啶 作用下， 生成 methyl 2-(3-chloropropanamido)benzoate
  参考文献：
  名称：

  Reisner; Ludwig; Simon, Arzneimittel-Forschung/Drug Research, 1977, vol. 27, # 4, p. 766 - 770

  摘要：

  DOI：

文献信息

• PIPERAZINE DERIVATIVE AND DRUG CONTAINING THE SAME
  申请人：ZERIA PHARMACEUTICAL CO., LTD.

  公开号：EP0598123A1

  公开（公告）日：1994-05-25

  A piperazine derivative represented by general formula (I) and a salt thereof, wherein B represents phenyl or pyridyl; m represents an integer of 2 or 3; p represents an integer of 1 or 2; R¹ represents hydrogen or halogen; and A represents -COOR², -Y-(CH₂)n-R³, (a), (b) or (c), wherein R² represents hydrogen or lower alkyl, Y represents sulfur, oxygen, NH or <-CONH- wherein <- represents a linkage with (CH₂)m; n represents an integer of 0 to 3; R³ represents cyano, amino, hydroxymethyl, 1H-tetrazolyl, 1-imidazolylcarbonyl, etc.; X represents CH or nitrogen; and R⁶ represents hydrogen or lower alkoxy. The compound has potent antihistaminic and antiallergic activities and high safety, and hence is excellent as antihistaminic, antiallergic and antiasthmatic drugs.

  通式(I)代表的哌嗪衍生物及其盐，其中 B 代表苯基或吡啶基；m 代表 2 或 3 的整数；p 代表 1 或 2 的整数；R¹ 代表氢或卤素；和 A 代表-COOR²、-Y-(CH₂)n-R³、(a)、(b)或(c)，其中 R² 代表氢或低级烷基，Y 代表硫、氧、NH 或 <-CONH- 其中 <- 代表与 (CH₂)m 连接；n 代表 0 至 3 的整数；R³ 代表氰基、氨基、羟甲基、1H-四唑基、1-咪唑羰基等。X 代表 CH 或氮；R⁶ 代表氢或低级烷氧基。该化合物具有很强的抗组胺和抗过敏活性，安全性高，因此是抗组胺、抗过敏和抗哮喘药物的极佳选择。
• Discovery of new potent protein arginine methyltransferase 5 (PRMT5) inhibitors by assembly of key pharmacophores from known inhibitors
  作者：Kongkai Zhu、Jia-Li Song、Hong-Rui Tao、Zhi-Qiang Cheng、Cheng-Shi Jiang、Hua Zhang

  DOI：10.1016/j.bmcl.2018.10.026

  日期：2018.12

  Protein arginine methyltransferase 5 (PRMT5) is an epigenetics related enzyme that has been validated as a promising therapeutic target for human cancer. Up to now, two small molecule PRMT5 inhibitors has been put into phase I clinical trial. In the present study, a series of candidate molecules were designed by combining key pharmacophores of formerly reported PRMT5 inhibitors. The in vitro PRMT5 inhibitory testing of compound 4b14 revealed an IC50 of 2.71 mu M, exhibiting high selectivity over PRMT1 and PRMT4 (> 70-fold selective). As expected, 4b14 exhibited potent anti-proliferative activity against a panel of leukemia and lymphoma cells, including MV4-11, Pfeiffer, SU-DHL-4 and KARPAS-422. Besides, 4b14 showed significant cell cycle arrest and apoptosis-inducing effects, as well as reduced the cellular symmetric arginine dimethylation level of SmD3 protein. Finally, affinity profiling analysis indicated that hydrophobic interactions, pi-pi stacking and cation-pi actions made the major contributions to the overall binding affinity. This scaffold provides a new chemical template for further development of better lead compounds targeting PRMT5.
• J. Heterocyclic Chem. 1987, 24, 175-180
  作者：

  DOI：——

  日期：——
• SINGH P., J. INDIAN CHEM. SOC., 1979, 56, NO 1, 77-80
  作者：SINGH P.

  DOI：——

  日期：——
• REISNER D. B.; LUDWIG B. J.; SIMON E.; DEJNEKA T.; SOFIA R. D., ARZNEIMITTEL-FORSCH. <ARZN-AD>, 1977, 27 NO 4, 766-770
  作者：REISNER D. B.、 LUDWIG B. J.、 SIMON E.、 DEJNEKA T.、 SOFIA R. D.

  DOI：——

  日期：——