3-amino-4-phenylthio-1,8-naphthalic anhydride | 97606-27-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-amino-4-phenylthio-1,8-naphthalic anhydride
• 英文别名: 7-Amino-8-phenylsulfanyl-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene-2,4-dione
• CAS: 97606-27-4
• 化学式: C₁₈H₁₁NO₃S
• 分子量: 321.356
• InChiKey: JVZLCWGLASJHLK-UHFFFAOYSA-N

物化性质

• 熔点：
  224-225 °C(Solv: pyridine (110-86-1))
• 沸点：
  600.9±50.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-amino-4-phenylthio-1,8-naphthalic anhydride 在 铜 、 溶剂黄146 、 sodium nitrite 作用下， 以 溶剂黄146 为溶剂， 生成 苯并噻吨二羧酸酐
  参考文献：
  名称：

  Synthesis and properties of benzothioxanthene dicarboximide hydroperoxide: an efficient ‘time-resolved’ DNA photocleaver with long-wavelength

  摘要：

  A novel hydroperoxide of benzothioxanthene dicarboximide B4 was synthesized through naphthyl radical-induced aromatic 1.5-hydrogen transfer in all unusual Pschorr cyclization and photooxygenation. It vas evaluated as all excellent 'time-resolved' DNA photocleaver with long-wavelength absorption, which can photonick the duplex DNA at a micromolar concentration of 5 muM upon irradiation at 450 nm. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(02)00442-2
• 作为产物：
  描述：

  3-nitro-4-phenylthio-1,8-naphthalic anhydride 在 盐酸 、 tin(II) chloride dihdyrate 作用下， 以 水 为溶剂， 反应 3.0h， 以80%的产率得到3-amino-4-phenylthio-1,8-naphthalic anhydride
  参考文献：
  名称：

  One small molecule as a theranostic agent: naphthalimide dye for subcellular fluorescence localization and photodynamic therapy in vivo

  摘要：

  基于萘酰亚胺的小分子治疗诊断剂已经研发出来，具有明亮的荧光成像和有效的光动力治疗效果。

  DOI：

  10.1039/c6md00104a

文献信息

• 一种苯并噻吩并萘酰亚胺衍生物及其合成工艺和应用
  申请人：浙江工业大学

  公开号：CN114702509A

  公开（公告）日：2022-07-05

  本发明公开了一种苯并噻吩并萘酰亚胺衍生物及其合成工艺和应用，所述苯并噻吩并萘酰亚胺衍生物的合成路线是，以4‑溴‑1,8‑萘酐为起始底物，经过硝化、芳环取代、还原反应、重氮化、Pschorr环合获得重要中间体‑‑苯并噻吩并萘酐中间体，然后这个中间体与不同的胺反应得到目标产物，然后与氯化氢气体反应制成对应化合物盐酸盐的形式。所有目标化合物经1H‑NMR、质谱等结构鉴定。这些化合物通过CCK‑8，细胞划痕实验技术和细胞克隆实验技术评估其在细胞水平具有显著的抗肿瘤活性。这项发明对发现新的抗肿瘤小分子药物，尤其为1,8萘酰亚胺衍生物的临床药物研发提供了方向。
• Synthesis, antitumor and DNA photocleaving activities of novel naphthalene carboxamides: effects of different thio-heterocyclic rings and aminoalkyl side chains
  作者：Zhigang Li、Qing Yang、Xuhong Qian

  DOI：10.1016/j.tet.2005.06.097

  日期：2005.9

  Two kinds of thio-heterocyclic fused naphthalene carboxamides, 3a-b, 4a-b, were designed, synthesized and quantitatively evaluated as efficient antitumor and DNA photocleaving agents. Compound 3a or 3b, having the thiophene ring, intercalated into DNA more strongly than compound 4a or 4b, having the thioxanthene ring. Compound 4a or 4b, photocleaved DNA more efficiently than 3a or 3b via superoxide anion. Compound 4a was the strongest inhibitor for P388 (murine leukemia cell), while 3a was the most cytotoxic one against A549 (human lung cancer cell). Each new compound showed stronger DNA photocleaving activity than corresponding naphthalimide. (c) 2005 Elsevier Ltd. All rights reserved.
• Five-member thio-heterocyclic fused naphthalimides with aminoalkyl side chains: intercalation and photocleavage to DNA
  作者：Yufang Xu、Baoyuan Qu、Xuhong Qian、Yonggang Li

  DOI：10.1016/j.bmcl.2004.12.011

  日期：2005.2

  Novel five-member thio-heterocyclic fused naphthalimides with aminoalkyl side chains were designed, synthesized and evaluated. These compounds have high Scatchard binding constants. They could damage DNA (supercoiled pBR322) from form I (closed) to II (nicked) at a concentration as low as 10 muM and from form I to form III at a concentration of 50 muM. The results implied that the influence of intercalating ability of chromophores on photocleaving ability of photocleavers depended on the mechanism of photocleavage. (C) 2004 Elsevier Ltd. All rights reserved.
• Naphthalimide intercalators with chiral amino side chains: Effects of chirality on DNA binding, photodamage and antitumor cytotoxicity
  作者：Qing Yang、Peng Yang、Xuhong Qian、Lianpeng Tong

  DOI：10.1016/j.bmcl.2008.09.104

  日期：2008.12

  Several novel heterocyclic-fused naphthalimides intercalators with chiral amino side chains were investigated. Their side chains' chiral configuration determines DNA binding activities in the order: S-enantiomers > R-enantiomers. And their DNA photodamaging activities were in good agreement with their DNA binding constants, the S-enantiomers could photocleave circular supercoiled pBR322 DNA more ef.ciently than their R-enantiomers. S-enantiomer B-3 could photodamage DNA at 0.2 mu M and cleave supercoiled plasmid DNA from form I to form II completely at 50 mu M. Almost all of these intercalators showed effective cytoxicities against human lung cancer cells and murine leukemia cells. S-enantiomers showed different antitumor cytotoxicity by comparison with R-enantiomers. This work may provide additional information for the role of amino side chains on intercalators as antitumor agents. (C) 2008 Elsevier Ltd. All rights reserved.
• Novel and highly efficient DNA photocleavers: hydroperoxides of heterocyclic-fused naphthalimides
  作者：Wei Yao、Xuhong Qian、Qingyan Hu

  DOI：10.1016/s0040-4039(00)01304-6

  日期：2000.9

  A series of novel hydroperoxides of heterocyclic-fused naphthalimides were designed, synthesized and exhibited excellent DNA photonicking activities. Among these compounds, the benzothiophenonaphthalimide-type reagent proved to be the most efficient, it can induce single-strand nicks in duplex DNA at micromolar concentration upon illumination. The relationship between the molecular structure and cleaving activities was discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.