3-(nitrooxy)cyclobutane-1,1-dicarboxylic acid | 1421354-47-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(nitrooxy)cyclobutane-1,1-dicarboxylic acid
• 英文别名: 3-Nitrooxycyclobutane-1,1-dicarboxylic acid；3-nitrooxycyclobutane-1,1-dicarboxylic acid
• CAS: 1421354-47-3
• 化学式: C₆H₇NO₇
• 分子量: 205.124
• InChiKey: CZVRLJBPGSHWAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(nitrooxy)cyclobutane-1,1-dicarboxylic acid 、 amino(cyclopentylamino)dihydroxyplatinum(VI) 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 以0.31 g的产率得到cis-[Pt(cyclopentylamine)(NH3)(3-(nitroxy)cyclobutane-1,1-dicarboxylate)2]
  参考文献：
  名称：

  Synthesis and biological evaluation of mixed ammine/amine platinum(II) complexes with dicarboxylate containing organic nitrate as ligand

  摘要：

  Two novel platinum(II) complexes cis-[Pt(L')(NH3)X] (where L' = cyclopentylamine or cyclohexylamine, X = 3-(nitrooxy)cyclobutane-1,1-dicarboxylate) were synthesized and spectrally characterized in this study. The purity of complexes 1 and 2 were studied by HPLC-MS spectra, and the contents of complexes 1 and 2 were more than 98%. It was demonstrated that the newly synthesized compounds with dicarboxylate containing organic nitrate as ligand possessed DNA unwinding capability similar to cisplatin by the means of agarose gel electrophoresis. In addition, the antiproliferative study by WST-8 assay revealed that these platinum(II) complexes exhibited considerable cytotoxicity against tested cancer cell lines in vitro compared with positive agents (cisplatin, oxaliplatin and carboplatin), especially complex 1, showing higher in vitro antitumoractivity than oxaliplatin and carboplatin in SGC7901 and A549 cell lines. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.09.034
• 作为产物：
  描述：

  3-苄氧基环丁烷-1,1-二甲酸二乙酯 在 硫酸 、 palladium 10% on activated carbon 、 氢气 、 硝酸 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 50.0 ℃ 、2.03 MPa 条件下， 反应 12.0h， 生成 3-(nitrooxy)cyclobutane-1,1-dicarboxylic acid
  参考文献：
  名称：

  一氧化氮供体基铂配合物作为潜在的抗癌药

  摘要：

  结合力：研究了含有有机硝酸盐配体的铂络合物作为抗癌剂。该复合物在水溶液中稳定，显示出优于相应母体化合物（卡铂）的细胞毒性，因此表明硝酸盐基配体释放一氧化氮的能力与铂的能力之间存在有趣的协同作用。抑制DNA合成的部分（请参阅方案）。

  DOI：

  10.1002/chem.201201605

文献信息

• Antitumor platinum(II) complexes of N-monoalkyl 1R,2R-diamino-cyclohexanes with 3-(nitrooxy)cyclobutane-1,1-dicarboxylate as a leaving group
  作者：Jian Zhao、Shaohua Gou、Gang Xu、Lin Cheng

  DOI：10.1016/j.ejmech.2014.08.007

  日期：2014.10

  A series of platinum(II) complexes of N-monoalkyl-1R,2R-diaminocylclohexanes with 3-(nitrooxy) cyclobutane-1,1-dicarboxylate as a leaving group were synthesized and characterized by elemental analysis, IR, H-1, C-13 and Pt-195 NMR spectroscopy together with ESI-MS spectrometer. In vitro cytotoxicity study on these complexes indicated they have considerable cytotoxicity against the tested cancer cell lines. Notably, complexes 2, 4, 6 and 8 showed high cytotoxicity against human A549 and HCT-116 cancer cell lines. The DNA binding of the platinum-based complexes 1 and 3-5 studied by agarose gel electrophoresis was in accordance with cytotoxicity to some extent. Reactions between the corresponding aqua analogues of the resulting complexes and glutathione (GSH) were studied by kinetics method under pseudo-first-order conditions using UV-Vis spectrophotometric technique. The results indicated that the introduction of alkyl moieties in 1R,2R-diaminocyclohexane (1R,2R-DACH) decreased the reaction rates of the aqua analogues of complexes 3-5 and GSH under the tested condition. Moreover, the stability of complex 8 was investigated by HPLC MS technique at different time in 36 h. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Nitric Oxide Donor-Based Platinum Complexes as Potential Anticancer Agents
  作者：Jian Zhao、Shaohua Gou、Yanyan Sun、Runting Yin、Zhimei Wang

  DOI：10.1002/chem.201201605

  日期：2012.11.5

  complexes containing organic nitrate ligands were investigated as anticancer agents. The complexes, which were stable in aqueous solution, showed cytotoxicity that was superior to that of the corresponding parent compound (carboplatin), thus suggesting an interesting synergy between the ability of the nitrate‐based ligands to release nitric oxide and the ability of the platinum moiety to inhibit DNA synthesis

  结合力：研究了含有有机硝酸盐配体的铂络合物作为抗癌剂。该复合物在水溶液中稳定，显示出优于相应母体化合物（卡铂）的细胞毒性，因此表明硝酸盐基配体释放一氧化氮的能力与铂的能力之间存在有趣的协同作用。抑制DNA合成的部分（请参阅方案）。
• Synthesis and biological evaluation of mixed ammine/amine platinum(II) complexes with dicarboxylate containing organic nitrate as ligand
  作者：Jian Zhao、Shaohua Gou、Gang Xu

  DOI：10.1016/j.ica.2013.09.034

  日期：2014.1

  Two novel platinum(II) complexes cis-[Pt(L')(NH3)X] (where L' = cyclopentylamine or cyclohexylamine, X = 3-(nitrooxy)cyclobutane-1,1-dicarboxylate) were synthesized and spectrally characterized in this study. The purity of complexes 1 and 2 were studied by HPLC-MS spectra, and the contents of complexes 1 and 2 were more than 98%. It was demonstrated that the newly synthesized compounds with dicarboxylate containing organic nitrate as ligand possessed DNA unwinding capability similar to cisplatin by the means of agarose gel electrophoresis. In addition, the antiproliferative study by WST-8 assay revealed that these platinum(II) complexes exhibited considerable cytotoxicity against tested cancer cell lines in vitro compared with positive agents (cisplatin, oxaliplatin and carboplatin), especially complex 1, showing higher in vitro antitumoractivity than oxaliplatin and carboplatin in SGC7901 and A549 cell lines. (C) 2013 Elsevier B.V. All rights reserved.