4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl 2-((4-(nitrooxy)butanoyl)oxy)benzoate | 1357362-67-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl 2-((4-(nitrooxy)butanoyl)oxy)benzoate
• 英文别名: NOSH-ASA；NOSH-aspirin；[4-(5-sulfanylidenedithiol-3-yl)phenyl] 2-(4-nitrooxybutanoyloxy)benzoate
• CAS: 1357362-67-4
• 化学式: C₂₀H₁₅NO₇S₃
• 分子量: 477.54
• InChiKey: CEDNXFMUAHDZQB-UHFFFAOYSA-N

物化性质

• 沸点：
  671.5±65.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  190
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  水杨醛 在 4-二甲氨基吡啶 、 potassium permanganate 、 silver nitrate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 21.0h， 生成 4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl 2-((4-(nitrooxy)butanoyl)oxy)benzoate
  参考文献：
  名称：

  NOSH-Aspirin: A Novel Nitric Oxide–Hydrogen Sulfide-Releasing Hybrid: A New Class of Anti-inflammatory Pharmaceuticals

  摘要：

  A series of new hybrids of aspirin (ASA), bearing both nitric oxide (NO) and hydrogen sulfide (H2S)-releasing moieties were synthesized and designated as NOSH compounds (1-4). NOSH-1 (4-(3-thioxo-3H-1,2-dithiol-5-yl) phenyl 24(4-(nitrooxy)butanoyl)oxy) benzoate); NOSH-2 (4-(nitrooxy)butyl (2-((4-(3-thioxo-3H-1,2-dithiol-5-yl)phenoxy)carbonyl)phenyl)); NOSH-3 (4-carbamothioylphenyl 2-((4-(nitrooxy)butanoyl)oxy)benzoate); and NOSH-4 (4-(nitrooxy)butyl 2-(5-((R)-1,2-dithiolan-3-yl)pentanoyloxy)benzoate). The cell growth inhibitory properties of compounds 1-4 were evaluated in eleven different human cancer cell lines of six different tissue origins. These cell lines are of adenomatous (colon, pancreatic, lung, prostate), epithelial (breast), and lymphocytic (leukemia) origin. All NOSH compounds were extremely effective in inhibiting the growth of these cell lines. NOSH-1 was the most potent, with an IC50 of 48 +/- 3 nM in HT-29 colon cancer cells. This is the first NSAID-based compound with such potency. This compound was also devoid of any cellular toxicity, as determined by LDH release. NOSH-1 was comparable to aspirin in its anti-inflammatory properties, using the carrageenan rat paw edema model.

  DOI：

  10.1021/ml300002m

文献信息

• NO- and H2S-releasing compounds
  申请人：RESEARCH FOUNDATION OF THE CITY UNIVERSITY OF NEW YORK

  公开号：US10450260B2

  公开（公告）日：2019-10-22

  This disclosure relates to compounds containing both an NO-releasing moiety and an H2S-releasing moiety and the use of such compounds in treating inflammatory diseases, including cancers.

  本公开涉及同时含有释放 NO 的分子和释放 H2S 的分子的化合物，以及此类化合物在治疗炎症性疾病（包括癌症）中的应用。
• NO- AND H2S- RELEASING COMPOUNDS
  申请人：Research Foundation Of The City University Of New York

  公开号：EP2744487B1

  公开（公告）日：2016-10-05
• [EN] NO- AND H2S- RELEASING COMPOUNDS<br/>[FR] COMPOSÉS LIBÉRANT NO ET H2S
  申请人：UNIV CITY NEW YORK RES FOUND

  公开号：WO2013025790A3

  公开（公告）日：2013-05-10
• NOVEL SYNTHETIC ANTIOXIDANTS AND THEIR USES
  申请人：Lu Yansong

  公开号：US20150336884A1

  公开（公告）日：2015-11-26

  The present invention relates to synthetic organic antioxidants of small molecules. The novel dithiol-containing compounds in this invention possess strongest possible capability as both scavenger for free radicals and antioxidant. This invention is directed to novel molecules as prodrugs of the novel dithiol-containing compounds, their rational design, their feasible preparation route by means of synthetic organic chemistry, and their potential uses in application to treatment and/or prevention of major diseases associated with oxidative stress, such as Alzheimer's disease, Parkinson's disease, cancer, diabetes, HIV, acne, cardiovascular disease, renal disease, hypertension, hypercholesterolemia, hyperlipidemia, rheumatoid arthritis, inflammation, pain, aging, stroke, cataract, glaucoma, age-related macular degeneration, etc.
• Method of Priming Plants Against Abiotic Stress Factors
  申请人：Research Foundation of the City University of New York

  公开号：US20170174651A1

  公开（公告）日：2017-06-22

  A method of reducing cellular damage to a plant by treating the plant with a compound containing an NO-releasing moiety and an H 2 S-releasing moiety covalently bonded to an aspirin derived core or a NOSH compound is claimed. The compounds may also be used in a method of priming a plant against abiotic stress factors and a method of promoting plant growth.