4-nitrooxymethylbenzoyl chloride

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-nitrooxymethylbenzoyl chloride
• 英文别名: 3-((nitrooxy)methyl)benzoyl chloride；(4-Carbonochloridoylphenyl)methyl nitrate
• 化学式: C₈H₆ClNO₄
• 分子量: 215.593
• InChiKey: UELBBICIIRBQJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-半胱氨酸乙酯盐酸盐 、 4-nitrooxymethylbenzoyl chloride 在 sodium acetate 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 ethyl (2R)-2-[[4-(nitrooxymethyl)benzoyl]amino]-3-sulfanylpropanoate
  参考文献：
  名称：

  NO-Donors (VII [1]): Synthesis and Cyclooxygenase Inhibitory Properties of N-and S-Nitrooxypivaloyl-cysteine Derivatives of Naproxen — A Novel Type of NO-NSAID

  摘要：

  Nitric oxide (NO) has been reported to subserve many of the same mucosal protection mechanisms as prostaglandins and is sufficient for acute gastroprotection and ulcer healing. In fact, NO-donating NSAID hybrid compounds such as the nitrooxybutyl ester of naproxen show reduced ulcerogenic activity while maintaining anti-inflammatory activity. We introduce two prototypes of novel triple-hybrid compounds consisting of cysteine which is known to enhance the activity of organic nitrates and to reduce nitrate tolerance, an NSAID (naproxen), and an organic nitrate (nitrooxypivaloic acid). L-Cysteine ethyl ester first was N-acylated in a CH2Cl2/H2O two-phase system using the acid chlorides of naproxen or nitrooxypivaloic acid, respectively, and sodium acetate, or alternatively using the DCC-activated nitrooxy acid in absolute CH2Cl2. The N-acylated intermediates were subsequently S-acylated using the acid chlorides or alternatively the carbonyldiimidazole (CDI)-activated acids again. The two naproxon-cysteine-nitrate hybrid prodrugs were screened in vitro for their cyclooxygenase inhibitory properties relative to naproxen. In this screening the N-nitrooxyacylcysteine derivative was found to be inactive in the concentration range of 0.1-10 mumol/L against both COX-1 and COX-2, while the S-nitrooxyacylcysteine derivative had only weak activity against COX-1.

  DOI：

  10.1002/1521-4184(200211)335:8<363::aid-ardp363>3.0.co;2-s
• 作为产物：
  描述：

  4-[(nitrooxy)methyl]benzoic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-nitrooxymethylbenzoyl chloride
  参考文献：
  名称：

  ROCK激酶抑制剂的硝基氧衍生物

  摘要：

  本发明提供了一种NO供体的小分子化合物，其特征在于：为由如下结构式I所示的化合物或其立体异构体，几何异构体，互变异构体，消旋体，氘代同位素衍生物，水合物，溶剂化物，代谢产物以及药学上可接受的盐或前药；其中，环A为取代或未取代的杂芳环；X选自(CH2)n，其中n选自0、1、2、3；R为末端‑O‑NO2的取代基；R1选自氢、羟基、卤素、氨基、氰基、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的烯基，取代或未取代的炔基，取代或未取代的杂烷基；R2、R3分别独立地选自氢、取代或未取代的烷基、取代或未取代的环烷基、氨基保护基；或者，R2与R3相连构成取代或未取代的环杂烷基。该化合物对ROCK激酶有高活性的抑制作用。

  公开号：

  CN111217834B

文献信息

• Methods of making 21-[4'-(nitrooxyalkyl)benzoate] corticosteroid derivatives and intermediates useful in the synthesis thereof
  申请人：——

  公开号：US20030153545A1

  公开（公告）日：2003-08-14

  The present invention provides methods of making 21-[4′-(nitrooxyalkyl)benzoate] corticosteroid derivatives according to the following general reaction scheme: 1 The invention also provides intermediates useful in making such 21-[4′-(nitrooxyalkyl)benzoate] corticosteroid derivatives as well as methods for making such intermediates.

  本发明提供了根据以下一般反应方案制备21-[4'-(硝基氧烷基)苯甲酸酯]糖皮质激素衍生物的方法。该发明还提供了在制备这种21-[4'-(硝基氧烷基)苯甲酸酯]糖皮质激素衍生物中有用的中间体，以及制备这种中间体的方法。
• METHODS OF MAKING 21- 4'-(NITROOXYALKYL) BENZOATE CORTICOSTEROID DERIVATIVES AND INTERMEDIATES USEFUL IN THE SYNTHESIS THEREOF
  申请人：Nicox S.A.

  公开号：EP1395544B1

  公开（公告）日：2012-01-04
• US6696592B2
  申请人：——

  公开号：US6696592B2

  公开（公告）日：2004-02-24
• [EN] METHOD OF PURIFYING POLYCYCLIC DYES<br/>[FR] METHODE DE PURIFICATION DE COLORANTS POLYCYCLIQUES
  申请人：OPTIVA INC

  公开号：WO2002094942A1

  公开（公告）日：2002-11-28

  The disclosed invention pertains to technology of fabricating and purifying synthetic dyes and may be used in various areas of industry and national economy, particularly in fabrication of materials for polarizing coatings of various purposes. In this method of purifying polycyclic dyes, the original dye is processed at least once with concentrated hydrochloric acid in the presence of at least one nitrogen-containing organic compound, such as heterocyclic base and/or aliphatic and/or aromatic amine, and/or quaternary ammonium salt in the amount of 0.1-5% of the weight of the dye at 50-100°C with subsequent filtration. After that, the obtained press-cake is processed at least once with boiling glacial ascetic acid with subsequent hot filtration of the suspension. Obtained sediment is washed with distilled water, after which the sediment is repulped in water, filtered and dried.
• ROCK激酶抑制剂的硝基氧衍生物
  申请人：维眸生物科技（上海）有限公司

  公开号：CN111217834B

  公开（公告）日：2021-10-26

  本发明提供了一种NO供体的小分子化合物，其特征在于：为由如下结构式I所示的化合物或其立体异构体，几何异构体，互变异构体，消旋体，氘代同位素衍生物，水合物，溶剂化物，代谢产物以及药学上可接受的盐或前药；其中，环A为取代或未取代的杂芳环；X选自(CH2)n，其中n选自0、1、2、3；R为末端‑O‑NO2的取代基；R1选自氢、羟基、卤素、氨基、氰基、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的烯基，取代或未取代的炔基，取代或未取代的杂烷基；R2、R3分别独立地选自氢、取代或未取代的烷基、取代或未取代的环烷基、氨基保护基；或者，R2与R3相连构成取代或未取代的环杂烷基。该化合物对ROCK激酶有高活性的抑制作用。