[1-bromo-6-(cycloheptylcarbamoyl)naphthalen-2-yl] N,N-dimethylcarbamate | 1397274-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [1-bromo-6-(cycloheptylcarbamoyl)naphthalen-2-yl] N,N-dimethylcarbamate
• CAS: 1397274-68-8
• 化学式: C₂₁H₂₅BrN₂O₃
• 分子量: 433.345
• InChiKey: NPULQJZGBKKQID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-羟基-2-萘甲酯 在 N-溴代丁二酰亚胺(NBS) 、 水 、 caesium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 144.0h， 生成 [1-bromo-6-(cycloheptylcarbamoyl)naphthalen-2-yl] N,N-dimethylcarbamate
  参考文献：
  名称：

  Synthesis and structure–activity relationship of (1-halo-2-naphthyl) carbamate-based inhibitors of KIAA1363 (NCEH1/AADACL1)

  摘要：

  KIAA1363 is a serine hydrolase whose activity has been shown to be positively associated with tumor cell invasiveness. Thus, inhibitors of KIAA1363 represent a novel targeted therapy approach towards cancer. AX11890 ((1-bromo-2-naphthyl) N,N-dimethylcarbamate) was identified as a KIAA1363 inhibitor with an IC50 value of 1.2 mu M and was shown using ESI-MS to carbamylate the catalytic residue Ser(191). SAR studies explored both substitution of the 1-bromo group and derivatization of the 6-position. Activity-based protein profiling demonstrated AX13057 inhibited tumor-localized KIAA1363 in SK-OV-3 xenograft-bearing mice. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.05.102

文献信息

• Synthesis and structure–activity relationship of (1-halo-2-naphthyl) carbamate-based inhibitors of KIAA1363 (NCEH1/AADACL1)
  作者：Kevin R. Shreder、Emme C.K. Lin、Jiangyue Wu、Julia Cajica、Christopher M. Amantea、Yi Hu、Eric Okerberg、Heidi E. Brown、Lan M. Pham、De Michael Chung、Allister S. Fraser、Ethel McGee、Jonathan S. Rosenblum、John W. Kozarich

  DOI：10.1016/j.bmcl.2012.05.102

  日期：2012.9

  KIAA1363 is a serine hydrolase whose activity has been shown to be positively associated with tumor cell invasiveness. Thus, inhibitors of KIAA1363 represent a novel targeted therapy approach towards cancer. AX11890 ((1-bromo-2-naphthyl) N,N-dimethylcarbamate) was identified as a KIAA1363 inhibitor with an IC50 value of 1.2 mu M and was shown using ESI-MS to carbamylate the catalytic residue Ser(191). SAR studies explored both substitution of the 1-bromo group and derivatization of the 6-position. Activity-based protein profiling demonstrated AX13057 inhibited tumor-localized KIAA1363 in SK-OV-3 xenograft-bearing mice. (C) 2012 Published by Elsevier Ltd.