6-(甲硫基)-2-萘甲酸 | 885227-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 6-(甲硫基)-2-萘甲酸
• 英文名称: 6-(methylsulfanyl)-2-naphthoic acid
• 英文别名: 6-(methylthio)-2-naphthoic acid；6-methylsulfanylnaphthalene-2-carboxylic acid
• CAS: 885227-49-6
• 化学式: C₁₂H₁₀O₂S
• 分子量: 218.276
• InChiKey: NMPGHTGXLFQAPI-UHFFFAOYSA-N

物化性质

• 沸点：
  403.2±20.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(甲硫基)-2-萘甲酸 在 盐酸 、 bis(1,5-cyclooctadiene)nickel (0) 作用下， 以 水 、 甲苯 为溶剂， 反应 14.0h， 生成 2-萘甲酸
  参考文献：
  名称：

  惰性碳-硫键的无配体镍催化还原裂解

  摘要：

  提出了在无配体条件下C（sp 2）–和C（sp 3）–SMe键的催化还原裂解。该方法的特点是适用范围广，化学选择性高，包括具有挑战性的底物组合，可设计正交和位点选择性方法。

  DOI：

  10.1021/ol2033306
• 作为产物：
  描述：

  6-羟基-2-萘甲酯 在 三乙烯二胺 、 二苯醚 、 硫酸二甲酯 、 potassium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 6-(甲硫基)-2-萘甲酸
  参考文献：
  名称：

  Discovery and Mechanism Study of SIRT1 Activators that Promote the Deacetylation of Fluorophore-Labeled Substrate

  摘要：

  SIRT1 is an NAD(+)-dependent deacetylase, whose activators have potential therapeutic applications in age-related diseases. Here we report a new class of SIRT1 activators. The activation is dependent on the fluorophore labeled to the substrate. To elucidate the activation mechanism, we solved the crystal structure of SIRT3/ac-RHKKac-AMC complex. The structure revealed that the fluorophore blocked the H-bond formation and created a cavity between the substrate and the Rossmann fold. We built the SIRT1/ac-RHKKac-AMC complex model based on the crystal structure. K-m and K-d determinations demonstrated that the fluorophore decreased the peptide binding affinity. The binding modes of SIRT1 activators indicated that a portion of the activators interacts with the fluorophore through pi-stacking, while the portion inserts into the cavity or interacts with the Rossmann fold, thus increasing the substrate affinity. Our study provides new insights into the mechanism of SIRT1 activation and may aid the design of novel SIRT1 activators.

  DOI：

  10.1021/jm301032j

文献信息

• Nitrobenzindoles and Their use in Cancer Therapy
  申请人：Denny William Alexander

  公开号：US20080119442A1

  公开（公告）日：2008-05-22

  The present invention relates generally to nitro-1,2-dihydro-3H-benzo[e]indoles and related analogues, to their preparation, and to their use as hypoxia-selective drugs and radiosensitizers for cancer therapy, both alone or in combination with radiation and/or other anticancer drugs.

  本发明涉及硝基-1,2-二氢-3H-苯并[e]吲哚及其相关类似物，其制备方法以及其作为低氧选择性药物和放射增敏剂在癌症治疗中的使用，可以单独使用或与辐射和/或其他抗癌药物联合使用。
• Nitrobenzindoles and their use in cancer therapy
  申请人：Auckland Uniservices Limited

  公开号：US07718688B2

  公开（公告）日：2010-05-18

  The present invention relates generally to nitro-1,2-dihydro-3H-benzo[e]indoles and related analogues, to their preparation, and to their use as hypoxia-selective drugs and radiosensitizers for cancer therapy, both alone or in combination with radiation and/or other anticancer drugs.

  本发明涉及硝基-1,2-二氢-3H-苯并[e]吲哚及其相关类似物，其制备方法以及它们作为治疗癌症的低氧选择性药物和放射增敏剂的用途，无论是单独使用还是与放射线和/或其他抗癌药物联合使用。
• Urea-containing isoxazole derivatives as FXR agonists and methods of use thereof
  申请人：Enanta Pharmaceuticals, Inc.

  公开号：US10597391B2

  公开（公告）日：2020-03-24

  The present invention provides compounds of Formula I, Pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising these compounds and methods of using these compounds to prevent or treat FXR-mediated or TGR5-mediated diseases or conditions.

  本发明提供了式 I 的化合物、 其药学上可接受的盐、包含这些化合物的药物组合物以及使用这些化合物预防或治疗 FXR 介导或 TGR5 介导的疾病或病症的方法。
• WO2006/43839
  申请人：——

  公开号：——

  公开（公告）日：——
• Hypoxia-Activated Prodrugs: Substituent Effects on the Properties of Nitro <i>seco</i>-1,2,9,9a-Tetrahydrocyclopropa[<i>c</i>]benz[<i>e</i>]indol-4-one (nitroCBI) Prodrugs of DNA Minor Groove Alkylating Agents
  作者：Moana Tercel、Graham J. Atwell、Shangjin Yang、Ralph J. Stevenson、K. Jane Botting、Maruta Boyd、Eileen Smith、Robert F. Anderson、William A. Denny、William R. Wilson、Frederik B. Pruijn

  DOI：10.1021/jm901202b

  日期：2009.11.26

  Nitrochloromethylbenzindolines (nitroCBIs) are a new class of hypoxia-activated prodrugs for antitumor therapy. The recently reported prototypes undergo hypoxia-selective metabolism to form potent DNA minor groove alkylating agents and are selectively toxic to some but not all hypoxic tumor cell lines. Here we report a series of 31 analogues that bear an extra electron-withdrawing substituent that serves to raise the one-electron reduction potential of the nitroCBI. We identify a subset of compounds, those with a basic side chain and sulfonamide or carboxamide substituent, that have consistently high hypoxic selectivity. The best of these, with a 7-sulfonamide substituent, displays hypoxic cytotoxicity ratios of 275 and 330 in Skov3 and HT29 human tumor cell lines, respectively. This compound (28) is efficiently and selectively metabolized to the corresponding aminoCBI, is selectively cytotoxic tinder hypoxia in all 11 cell lines examined, and demonstrates activity against hypoxic tumor cells in a human tumor xenograft in vivo.