4-溴-3-硝基-1-萘酸 | 852381-11-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-溴-3-硝基-1-萘酸
• 英文名称: 4-bromo-3-nitro-1-naphthoic acid
• 英文别名: 4-bromo-3-nitronaphthalene-1-carboxylic acid
• CAS: 852381-11-4
• 化学式: C₁₁H₆BrNO₄
• 分子量: 296.077
• InChiKey: JMWKCZADLCMYID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-溴-3-硝基-1-萘酸 在 溶剂黄146 、 sodium disulfide 作用下， 以 水 为溶剂， 反应 12.5h， 生成 2-phenylnaphtho[2,1-d]thiazole-5-carboxylic acid
  参考文献：
  名称：

  Novel heterocyclic family of phenyl naphthothiazole carboxamides derived from naphthalimides: synthesis, antitumor evaluation, and DNA photocleavage

  摘要：

  A new heterocyclic family of (2-(dimethylamino)ethyl)-2-substituted phenylnaphtho[2, 1-d]thiazole-5-carboxamides modified from naphthalimides was designed, synthesized, and quantitatively evaluated as antitumor agents and photonucleases. All these compounds were found to be more cytotoxic against P388 than against A549. B-3 (m-NO2) was found to be the strongest inhibitor for P388 with IC50 of 1.49 mu M, while B-2 was the most cytotoxic compound against A549 with IC50 of 12 mu M. B-4 (p-CH3) the most efficient DNA photocleaver, showed detectable DNA cleavage at 0.5 mu M and total cleavage from form I to 100% form II at 50 mu M. The photocleaving mechanism was changed with the modification to be via superoxide anion and radical. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.045
• 作为产物：
  描述：

  4-溴-3-硝基-1,8-萘酐 在 溶剂黄146 、 mercury(II) oxide 、 盐酸 作用下， 以 水 为溶剂， 反应 99.0h， 生成 4-溴-3-硝基-1-萘酸 、 4-bromo-3-nitro-8-naphthoic acid
  参考文献：
  名称：

  Synthesis of thiazo- or thiadiazo- naphthalene carboxamides via mercuric intermediates and their antitumor and DNA photocleavage activities

  摘要：

  Two kinds of thiazo- or thiadiazo- naphthalene carboxamides with aminoalkyl side chains at 5- or 6-position modified from naphthalimides were designed, synthesized and quantitatively evaluated as antitumor and DNA photocleaving agents. The compound with aminoalkyl side chain at 6-position showed stronger antitumor (A549, P388) and DNA photocleaving abilities than its isomer with that at 5-position. B-2, the most efficient DNA photocleaver, also exhibited the highest cytotoxicity with the IC50 of 2.53 and 0.11 mu M against cell lines of A549 and P388, respectively. These compounds also photocleaved DNA more efficiently than their corresponding naphthalimides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.135

文献信息

• Synthesis of thiazo- or thiadiazo- naphthalene carboxamides via mercuric intermediates and their antitumor and DNA photocleavage activities
  作者：Zhigang Li、Qing Yang、Xuhong Qian

  DOI：10.1016/j.tet.2005.03.135

  日期：2005.7

  Two kinds of thiazo- or thiadiazo- naphthalene carboxamides with aminoalkyl side chains at 5- or 6-position modified from naphthalimides were designed, synthesized and quantitatively evaluated as antitumor and DNA photocleaving agents. The compound with aminoalkyl side chain at 6-position showed stronger antitumor (A549, P388) and DNA photocleaving abilities than its isomer with that at 5-position. B-2, the most efficient DNA photocleaver, also exhibited the highest cytotoxicity with the IC50 of 2.53 and 0.11 mu M against cell lines of A549 and P388, respectively. These compounds also photocleaved DNA more efficiently than their corresponding naphthalimides. (c) 2005 Elsevier Ltd. All rights reserved.
• Novel heterocyclic family of phenyl naphthothiazole carboxamides derived from naphthalimides: synthesis, antitumor evaluation, and DNA photocleavage
  作者：Zhigang Li、Qing Yang、Xuhong Qian

  DOI：10.1016/j.bmc.2005.02.045

  日期：2005.5

  A new heterocyclic family of (2-(dimethylamino)ethyl)-2-substituted phenylnaphtho[2, 1-d]thiazole-5-carboxamides modified from naphthalimides was designed, synthesized, and quantitatively evaluated as antitumor agents and photonucleases. All these compounds were found to be more cytotoxic against P388 than against A549. B-3 (m-NO2) was found to be the strongest inhibitor for P388 with IC50 of 1.49 mu M, while B-2 was the most cytotoxic compound against A549 with IC50 of 12 mu M. B-4 (p-CH3) the most efficient DNA photocleaver, showed detectable DNA cleavage at 0.5 mu M and total cleavage from form I to 100% form II at 50 mu M. The photocleaving mechanism was changed with the modification to be via superoxide anion and radical. (c) 2005 Elsevier Ltd. All rights reserved.