3-(3-nitrophenyl)-1,2,4-oxadiazol-5-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(3-nitrophenyl)-1,2,4-oxadiazol-5-ol
• 英文别名: 3-(3-Nitrophenyl)-4,5-dihydro-1,2,4-oxadiazol-5-one；3-(3-nitrophenyl)-4H-1,2,4-oxadiazol-5-one
• 化学式: C₈H₅N₃O₄
• mdl: MFCD12774150
• 分子量: 207.145
• InChiKey: COXDLQHDPALXMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3-nitrophenyl)-1,2,4-oxadiazol-5-ol 在 吡啶 、 tin(II) chloride dihdyrate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hexamethyldisilazane 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 50.0h， 生成 N-(3-(5-((4-chloro-1H-indazol-5-yl)amino)-1,2,4-oxadiazol-3-yl)phenyl)-2-fluorobenzamide
  参考文献：
  名称：

  [EN] ROCK2 INHIBITORS AND USES THEREOF
  [FR] INHIBITEURS DE ROCK2 ET LEURS UTILISATIONS

  摘要：

  The present disclosure provides compounds of Formula (I) and (II), which may be R0CK2 inhibitors. The present disclosure also provides pharmaceutical compositions and kits comprising the compounds, and methods of treating or preventing diseases and disorders associated with R0CK2 (e.g., fibrotic disease, autoimmune disease, inflammatory-fibrotic condition, inflammatory condition, edema, ophthalmic disease, cardiovascular disease, central nervous system disorder, cancer) by administering to a subject in need thereof the compounds or pharmaceutical compositions.

  公开号：

  WO2023009475A1
• 作为产物：
  描述：

  间硝基苯腈 在 吡啶 、 盐酸羟胺 、 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 32.0h， 生成 3-(3-nitrophenyl)-1,2,4-oxadiazol-5-ol
  参考文献：
  名称：

  [EN] ROCK2 INHIBITORS AND USES THEREOF
  [FR] INHIBITEURS DE ROCK2 ET LEURS UTILISATIONS

  摘要：

  The present disclosure provides compounds of Formula (I) and (II), which may be R0CK2 inhibitors. The present disclosure also provides pharmaceutical compositions and kits comprising the compounds, and methods of treating or preventing diseases and disorders associated with R0CK2 (e.g., fibrotic disease, autoimmune disease, inflammatory-fibrotic condition, inflammatory condition, edema, ophthalmic disease, cardiovascular disease, central nervous system disorder, cancer) by administering to a subject in need thereof the compounds or pharmaceutical compositions.

  公开号：

  WO2023009475A1

文献信息

• <i>tert</i>-Butyl Nitrite Mediated Synthesis of 1,2,4-Oxadiazol-5(4<i>H</i>)-ones from Terminal Aryl Alkenes
  作者：Prasenjit Sau、Amitava Rakshit、Tipu Alam、Hemant Kumar Srivastava、Bhisma K. Patel

  DOI：10.1021/acs.orglett.9b01430

  日期：2019.7.5

  (TBN) mediated synthesis of 3-aryl-1,2,4-oxadiazol-5(4H)-ones has been accomplished using terminal aryl alkenes via a biradical reaction intermediate. Three consecutive sp2 C–H bond functionalizations of styrenes afforded 3-phenyl-1,2,4-oxadiazol-5(4H)-ones via the formation of new C═N, C═O, C–O, and two C–N bonds. Both of the N atoms originate from TBN, while the carbonyl oxygen is from the water (moisture)

  已使用末端芳基烯烃通过双自由基反应中间体完成了亚硝酸叔丁酯（TBN）介导的3-芳基-1,2,4-恶二唑-5（4 H）-的合成。苯乙烯的三个连续的sp 2 C–H键官能化通过形成新的C═N，C═O，C–O和两个生成3-苯基-1,2,4-恶二唑-5（4 H）-一。 C–N键。N个原子都来自TBN，而羰基氧则来自水（水分），其他氧则来自TBN的N = O部分。
• Heterocycles from nitrile oxides. 3. 1,2,4-Oxadiazol-5(4H)-ones
  作者：Ahmad Q. Hussein

  DOI：10.1021/je00047a037

  日期：1987.1
• HUSSELN AHMAD Q., J. CHEM. AND ENG. DATA, 32,(1987) N 1, 127-128
  作者：HUSSELN AHMAD Q.

  DOI：——

  日期：——
• New oxadiazol‐5‐ones derivatives and their performance as angiotensin‐converting enzyme (ACE) inhibitors
  作者：Larissa Fernanda Lima Ferreira、Ilária Martina Silva Lins、Sidney Gustavo Diniz Feitosa、Jivaldo Gonçalves Ferreira、Larissa Gonçalves Maciel、Alice Valença Araújo、Janaína Versiani dos Anjos

  DOI：10.1002/jhet.4835

  日期：2024.7

  Angiotensin‐converting enzyme inhibitors are widely used in treating arterial hypertension, acting on the renin‐angiotensin‐aldosterone system and controlling blood pressure. We present a novel, greener, and faster methodology to assess the 1,2,4‐oxadiazol‐5‐one ring and perform molecular modifications to obtain angiotensin‐converting enzyme (ACE) inhibitors using this heterocyclic core. Molecular docking simulations indicate that the tested compounds exhibited an affinity for the ACE binding site, with scores comparable to the commercial inhibitor lisinopril. However, in vitro assays revealed that the compounds were ineffective in inhibiting ACE activity. The lack of inhibition may be related to the compounds' more apolar nature. These results emphasize the importance of integrating computational and experimental approaches in developing new drugs, providing valuable insights for planning future studies to optimize the activity of synthesized compounds.