O²-(acetoxymethyl)-1-(cyclopentylamino)diazen-1-ium-1,2-diolate

• 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: O²-(acetoxymethyl)-1-(cyclopentylamino)diazen-1-ium-1,2-diolate
• 英文别名: AcOM-CPA/NO；(Acetyloxymethoxyamino)-cyclopentylimino-oxidoazanium；(acetyloxymethoxyamino)-cyclopentylimino-oxidoazanium
• 化学式: C₈H₁₅N₃O₄
• 分子量: 217.225
• InChiKey: KZSCSHGVFHBEMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  溴甲基乙酸酯 、 sodium 1-(N-cyclopentylamino)diazen-1-ium-1,2-diolate 以 四氢呋喃 、 二甲基亚砜 为溶剂， 以72%的产率得到O²-(acetoxymethyl)-1-(cyclopentylamino)diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  Analysis of the HNO and NO donating properties of alicyclic amine diazeniumdiolates

  摘要：

  Nitroxyl (HNO) donors have been shown to elicit a variety of pharmacological responses, ranging from tumoricidal effects to treatment of heart failure. Isopropylamine-based diazeniumdiolates have been shown to produce HNO on decomposition under physiological conditions. Herein, we report the synthesis and HNO release profiles of primary alicyclic amine-based diazeniumdiolates. These compounds extend the range of known diazeniumdiolate-based HNO donors. Acetoxymethyl ester-protected diazeniumdiolates were also synthesized to improve purification and cellular uptake. The acetoxymethyl derivative of cyclopentylamine diazeniumdiolate not only showed higher cytotoxicity toward cancer cells as compared to the parent anion but was also effective in combination with tamoxifen for targeting estrogen receptor alpha-negative breast cancer cells. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.niox.2014.08.013

文献信息

• Compositions and Methods of Diazeniumdiolate-based Prodrugs for Treating Cancer
  申请人：ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA

  公开号：US20170333456A1

  公开（公告）日：2017-11-23

  The present disclosure provides methods utilizing the diazeniumdiolate-based prodrugs for the treatment of cancer via various mechanisms and procedures. The disclosure also provides kits comprising the diazeniumdiolate-based prodrugs.