3-(2-nitrosophenyl)propionic acid | 1094772-18-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(2-nitrosophenyl)propionic acid
• 英文别名: 3-(2-nitrosophenyl)propanoic acid；o-nitrosophenylpropionic acid；2-nitrosophenylpropionic acid
• CAS: 1094772-18-5
• 化学式: C₉H₉NO₃
• 分子量: 179.175
• InChiKey: NTZNNJBTLUODGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  66.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-nitrosophenyl)propionic acid 在 4-二甲氨基吡啶 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl 4-[[2-[3-[2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethoxy]-3-oxopropyl]phenyl]diazenyl]benzoate
  参考文献：
  名称：

  Structure requirements for anaerobe processing of azo compounds: Implications for prodrug design

  摘要：

  This Letter generalizes the metabolism of the azo class of compounds by Clostridium perfringens, an anaerobe found in the human colon. A recently reported 5-aminosalicylic acid-based prednisolone prodrug was shown to release the drug when incubated with the bacteria, while the para-aminobenzoic acid (PABA) based analogue did not. Instead, it showed a new HPLC peak with a relatively close retention time to the parent which was identified by LCMS as the partially reduced hydrazine product. This Letter investigates azoreduction across a panel of substrates with varying degrees of electronic and steric similarity to the PABA-based compound. Azo compounds with an electron donating group on the azo-containing aromatic ring showed immediate disproportionation to their parent amines without any detection of hydrazine intermediates by HPLC. Compounds containing only electron withdrawing groups are partially and reversibly reduced to produce a stable detectable hydrazine. They do not disproportionate to their parent amines, but regenerate the parent azo compound. This incomplete reduction is relevant to the design of azo-based prodrugs and the toxicology of azo-based dyes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.014
• 作为产物：
  描述：

  3-(2-aminophenyl)propanoic acid 在 oxone(R) 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 3-(2-nitrosophenyl)propionic acid
  参考文献：
  名称：

  [EN] TARGETING DIAZO PRODRUGS FOR THE TREATMENT OF GASTROINTESTINAL DISEASES
  [FR] CIBLAGE DE PROMÉDICAMENTS DIAZO POUR LE TRAITEMENT DE MALADIES GASTRO-INTESTINALES

  摘要：

  本文提供了一种减少患者NFkB DNA结合活性的化合物、组合物和方法，包括向患者施用本申请的化合物或组合物的治疗有效量，以减少、缓解或治疗各种胃肠疾病，如炎症性肠病（IBD）。

  公开号：

  WO2009003970A1

文献信息

• Oxidative cleavage of hydroxamic acid promoted by sodium periodate
  作者：Changchun Yuan、Biao Du、Miao-Miao Xun、Bo Liu

  DOI：10.1016/j.tet.2017.03.073

  日期：2017.6

  A series of hydroxamic acids, involving aliphatic, aromatic and cyclic substrates, were transformed to the corresponding carboxylic acids through NaIO4-mediated oxidative cleavage in mild conditions. Esterification of these acids with TMSCHN2 could result in formation of the corresponding methyl ester. This methodology makes good compensation for the existing methods transforming amides to esters. Our

  在温和的条件下，通过NaIO 4介导的氧化裂解，将涉及脂肪族，芳香族和环状底物的一系列异羟肟酸转化为相应的羧酸。用TMSCHN 2酯化这些酸可能导致形成相应的甲酯。该方法学很好地补偿了将酰胺转化为酯的现有方法。我们的结果也为利用异羟肟酸作为有用的合成原料铺平了道路。
• Design, Synthesis, and Pharmacological Effects of a Cyclization-Activated Steroid Prodrug for Colon Targeting in Inflammatory Bowel Disease
  作者：Juan F. Márquez Ruiz、Gabor Radics、Henry Windle、Hugo O. Serra、Ana Luísa Simplício、Kinga Kedziora、Padraic G. Fallon、Dermot P. Kelleher、John F. Gilmer

  DOI：10.1021/jm8016317

  日期：2009.5.28

  colon causing severe systemic side effects. We report here on a novel prodrug approach to targeting corticosteroids to the colon. The design involves attaching a 21-ester group that suppresses absorption during transit to the colon. The prodrug is designed to be primed by colonic microflora liberating an amino ester that cyclizes releasing the steroid. One of the prodrugs 5b was as efficacious as prednisolone

  糖皮质激素用于治疗炎性肠病。其使用的限制是它们在到达结肠之前会先从GIT吸收，从而引起严重的全身性副作用。我们在这里报告了一种针对皮质类固醇靶向结肠的新型前药方法。该设计涉及连接一个21酯基团，该基团在转移到结肠的过程中会抑制吸收。前药被设计成通过结肠微生物区系释放，释放出环化释放类固醇的氨基酯。在鼠DSS模型中，前药5b之一与泼尼松龙一样有效，但是没有引起胸腺萎缩，胸腺萎缩是全身性类固醇作用的标志。
• 一类肠道裂解型共药及其制备和用途
  申请人：轶诺（浙江）药业有限公司

  公开号：CN113943312A

  公开（公告）日：2022-01-18

  本发明涉及一类肠道裂解型共药(Codrug)及其制备和用途，具体地，本发明提供了一种如式I所示的共药化合物。本发明还提供了使用这类化合物治疗胃肠道自身免疫性疾病、炎症性疾病和癌症的方法；以及用于制备这类化合物的方法和中间物。
• Targeting Prodrugs for the Treatment of Gastrointestinal Diseases
  申请人：Gilmer John Francis

  公开号：US20090082314A1

  公开（公告）日：2009-03-26

  Provided herein are compounds, compositions and methods for decreasing NFκB DNA-binding activity in a patient comprising administering of a therapeutically effective amount of a compound or composition of the application to the patient to reduce, alleviate or treat various gastrointestinal diseases, such as inflammatory bowel disease (IBD).

  本文提供了一种降低患者NFκB DNA结合活性的化合物、组合物和方法，包括将本申请的化合物或组合物以治疗有效量的方式给予患者，以减轻、缓解或治疗各种胃肠道疾病，如炎症性肠病（IBD）。
• Substituted Aromatic Carboxamide and Urea Derivatives as Vanilloid Receptor Ligands
  申请人：FRANK Robert

  公开号：US20110003795A1

  公开（公告）日：2011-01-06

  The invention relates to substituted aromatic carboxamide and urea derivatives, to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions.

  该发明涉及取代芳香族羧酰胺和脲衍生物，其制备过程，含有这些化合物的药物组合物以及利用这些化合物制备药物组合物的用途。