4-mercapto-3-amino-1,8-naphthalic anhydride | 852381-19-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-mercapto-3-amino-1,8-naphthalic anhydride
• 英文别名: 4-mercapto-3-aminonaphthylic anhydride；7-Amino-8-sulfanyl-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene-2,4-dione；7-amino-8-sulfanyl-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene-2,4-dione
• CAS: 852381-19-2
• 化学式: C₁₂H₇NO₃S
• 分子量: 245.258
• InChiKey: IAEHJWZXRWDRLV-UHFFFAOYSA-N

物化性质

• 沸点：
  561.6±40.0 °C(Predicted)
• 密度：
  1.618±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-mercapto-3-amino-1,8-naphthalic anhydride 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Novel thiazonaphthalimides as efficient antitumor and DNA photocleaving agents: Effects of intercalation, side chains, and substituent groups

  摘要：

  A series of novel antitumor and DNA photocleaving agents was designed and synthesized by fusing a (substituted) thiazole ring to the naphthalimide skeletons. C-1, the most active compound against A549. was about 10-fold more cytotoxic than the compound amonafide. A,. the most active compound against P388, was about 6-fold more cylotoxic than amonafide. C-2, the most efficient DNA intercalator, showed the strongest DNA photocleaving activity Via Superoxide anion produced under UV light at 360 nm. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.006
• 作为产物：
  描述：

  4-溴-3-硝基-1,8-萘酐 在 sodium disulfide 作用下， 反应 8.0h， 生成 4-mercapto-3-amino-1,8-naphthalic anhydride
  参考文献：
  名称：

  Synthesis, antitumor evaluation and DNA photocleaving activity of novel methylthiazonaphthalimides with aminoalkyl side chains

  摘要：

  A series of methylthiazonaphthalimides was synthesized and quantitatively evaluated as efficient DNA intercalators, antitumor agents and DNA photocleavers. A(1) showed both efficient antitumor activities against cell lines of A549 and P388 with IC50 Of 82.8 and 31 nM, respectively. A(3) was the strongest antitumor agent against A549 with the IC50 of 20.8 nM. A(2), the most efficient DNA intercalator, was found to be the strongest DNA photocleaver via superoxide anion. An explanation was given for the disaccord between antitumor and DNA photocleaving activities. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.012

文献信息

• Sulfur-containing naphthalimide derivatives
  申请人：Qian Xuhong

  公开号：US20060111367A1

  公开（公告）日：2006-05-25

  The invention discloses novel sulfur-containing naphthalimide derivatives, and the preparation and uses thereof. The conjugated plane of naphthalimide derivatives of the invention is enlarged by incorporating 5-or 6-membered heteroaromatic ring and/or introducing S heteroatom, thus increasing the anti-tumor activity of naphthalimide. The compounds of the invention displays significant inhibiting activities to the proliferation of various tumor cells such as human lung cancer, gastric cancer, liver cancer, leucocythemia and the like. The inhibition of cell proliferation is dose-dependent.

  本发明公开了新型含硫萘啶酰亚胺衍生物及其制备方法和用途。通过加入 5 或 6 元杂芳环和/或引入 S 杂原子，扩大了本发明萘啶酰亚胺衍生物的共轭平面，从而提高了萘啶酰亚胺的抗肿瘤活性。本发明的化合物对多种肿瘤细胞的增殖具有显著的抑制作用，如人类肺癌、胃癌、肝癌、白细胞增多症等。对细胞增殖的抑制作用与剂量有关。
• SULFUR-CONTAINING NAPHTHOYLIMIDE DERIVATIVES
  申请人：East China University of Science and Technology

  公开号：EP1626050B1

  公开（公告）日：2009-12-02
• Thiadiazole: A new family of intercalative photonuclease with electron transfer and radical mechanisms
  作者：Yonggang Li、Yufang Xu、Xuhong Qian、Baoyuan Qu

  DOI：10.1016/s0960-894x(03)00737-6

  日期：2003.10

  A new family of photonuclease, thiadiazole-naphthalimide were synthesized and evaluated. Thiadiazole group was incorporated for the first time. These compounds intercalated into DNA efficiently and damaged DNA as low as 10 muM photochemically. Mechanism experiment showed that electron transfer and radicals were involved. (C) 2003 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.
• SULFUR-CONTAINING NAPHTHALIMIDE DERIVATIVES
  申请人：Qian Xuhong

  公开号：US20080234287A1

  公开（公告）日：2008-09-25

  The invention discloses novel sulfur-containing naphthalimide derivatives, and the preparation and uses thereof. The conjugated plane of naphthalimide derivatives of the invention is enlarged by incorporating 5- or 6-membered heteroaromatic ring and/or introducing S heteroatom, thus increasing the anti-tumor activity of naphthalimide. The compounds of the invention displays significant inhibiting activities to the proliferation of various tumor cells such as human lung cancer, gastric cancer, liver cancer, leucocythemia and the like. The inhibition of cell proliferation is dose-dependent.