5-Bromo-6-(dimethylcarbamoyloxy)naphthalene-2-carboxylic acid | 1397274-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-Bromo-6-(dimethylcarbamoyloxy)naphthalene-2-carboxylic acid
• 英文别名: 5-bromo-6-(dimethylcarbamoyloxy)naphthalene-2-carboxylic acid
• CAS: 1397274-81-5
• 化学式: C₁₄H₁₂BrNO₄
• 分子量: 338.158
• InChiKey: ISVULQGWPFTULM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Bromo-6-(dimethylcarbamoyloxy)naphthalene-2-carboxylic acid 以 乙腈 为溶剂， 反应 72.0h， 生成 [1-bromo-6-(phenylcarbamoyl)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
• 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 为溶剂， 反应 72.0h， 生成 5-Bromo-6-(dimethylcarbamoyloxy)naphthalene-2-carboxylic acid
  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

• Three birds one stone: an enzyme-activatable theragnostic agent for fluorescence diagnosis, photodynamic and inhibitor therapies
  作者：Xiuxiu Yue、Benhua Wang、Minhuan Lan、Jiangli Fan、Xiangzhi Song、James W. Foley

  DOI：10.1039/d3cc00214d

  日期：——

  AX11890, an inhibitor of overexpressed enzyme, KIAA1363, in some breast cancers, was conjugated with a benzo[a]phenothiazinium photosensitizer to develop a tumor micro-environment-responsive photosensitizer NBS-L-AX. In normal cells, the special geometry of NBS-L-AX causes the fluorescence and photodynamic therapeutic (PDT) effect of NBS-L to be quenched. In cancer cells, when allowed to interact with the

  AX11890是一种在某些乳腺癌中过表达酶 KIAA1363 的抑制剂，它与苯并[ a ]吩噻嗪光敏剂偶联，开发出肿瘤微环境响应光敏剂NBS-L-AX。在正常细胞中， NBS-L-AX的特殊几何形状导致 NBS-L 的荧光和光动力治疗 (PDT) 效应被淬灭。在癌细胞中，当允许与酶 KIAA1363 相互作用时，NBS-L-AX的几何形状发生变化，使其变得荧光和光动力活性。因此， NBS-L-AX材料可作为乳腺癌的活化显像剂和PDT治疗剂。此外，NBS-L-AX对乳腺癌细胞也表现出选择性抑制作用。
• 一种KIAA1363酶靶向近红外荧光染料及其制备方法与应用
  申请人：大连理工大学宁波研究院

  公开号：CN117567348A

  公开（公告）日：2024-02-20

  本发明属于生物医用功能染料技术领域，尤其涉及一种KIAA1363酶靶向近红外荧光染料及其制备方法与应用，所述的KIAA1363酶靶向近红外荧光染料的激发波长约775nm，发射波长约810nm，具备较强组织穿透能力、较低组织自吸收和光散射，可通过靶向肿瘤过表达的KIAA1363酶选择性点亮肿瘤细胞，从而定位肿瘤病灶，为肿瘤切除手术提供清晰切缘。
• 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.