R16 | 791590-89-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: R16
• 英文别名: N-(N',N'-dimethylaminoethyl)benzo[b]thieno[2,1-c]naphthalimide；99TC0Y7Hir；14-[2-(dimethylamino)ethyl]-3-thia-14-azapentacyclo[10.7.1.02,10.04,9.016,20]icosa-1,4,6,8,10,12(20),16,18-octaene-13,15-dione
• CAS: 791590-89-1
• 化学式: C₂₂H₁₈N₂O₂S
• 分子量: 374.463
• InChiKey: SYGWYBOJXOGMRU-UHFFFAOYSA-N

物化性质

• 熔点：
  171-172 °C
• 沸点：
  586.8±30.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  R16 在 双氧水 作用下， 以 甲醇 为溶剂， 生成 2-(13,15-dioxo-3-thia-14-azapentacyclo[10.7.1.02,10.04,9.016,20]icosa-1,4,6,8,10,12(20),16,18-octaen-14-yl)-N,N-dimethylethanamine oxide
  参考文献：
  名称：

  Novel N-oxide of naphthalimides as prodrug leads against hypoxic solid tumor: Synthesis and biological evaluation

  摘要：

  Novel tertiary amine N-oxides of naphthalimides were designed and synthesized as potential anticancer agents against hypoxic solid tumors. Although their ctDNA-binding affinities and cytotoxic activities against usual tumor cell lines were lower than those of corresponding amines, the N-oxides All and A4 showed hypoxia preference activities against A375 cells in vitro and might be used as interesting candidates of prodrug leads in hypoxic tumor cells. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.015
• 作为产物：
  描述：

  4-溴-3-硝基-1,8-萘酐 在 吡啶 、 盐酸 、 硫酸 、 溶剂黄146 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 R16
  参考文献：
  名称：

  Five-member thio-heterocyclic fused naphthalimides with aminoalkyl side chains: intercalation and photocleavage to DNA

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2004.12.011

文献信息

• 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
• Novel aliphatic N-oxide of naphthalimides as fluorescent markers for hypoxic cells in solid tumor
  作者：Hong Yin、Weiping Zhu、Yufang Xu、Min Dai、Xuhong Qian、Yuanli Li、Jianwen Liu

  DOI：10.1016/j.ejmech.2011.04.040

  日期：2011.7

  A series of novel aliphatic N-oxide of naphthalimides (A1-A5) were designed and prepared. The N-O group was firstly introduced into the amine side chain tailed to planar naphthalimide chromophore as hypoxic bioreductive marker. Fluorescence image analysis showed that the compounds could be used as potential markers for hypoxic cells (V79) in vitro especially for A1 with 17 times hypoxic-oxic fluorescence differential, which was probably due to the bis-bioreduction mechanism. (C) 2011 Elsevier Masson SAS. 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.
• US7541463B2
  申请人：——

  公开号：US7541463B2

  公开（公告）日：2009-06-02
• 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.