5-sec-butylisoxazol-3-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: 5-sec-butylisoxazol-3-ol
• 英文别名: 5-Butan-2-yl-1,2-oxazol-3-one
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: UKGPMXDTSITCFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-sec-butylisoxazol-3-ol 、 二甲氨基甲酰氯 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 16.33h， 以82%的产率得到5-sec-butylisoxazol-3-yl dimethylcarbamate
  参考文献：
  名称：

  3-Oxoisoxazole-2(3H)-carboxamides and isoxazol-3-yl carbamates: Resistance-breaking acetylcholinesterase inhibitors targeting the malaria mosquito, Anopheles gambiae

  摘要：

  To identify potential selective and resistance-breaking mosquitocides against the African malaria vector Anopheles gambiae, we investigated the acetylcholinesterase (AChE) inhibitory and mosquitocidal properties of isoxazol-3-yl dimethylcarbamates (15), and the corresponding 3-oxoisoxazole-2(3H)-dimethylcarboxamide isomers (14). In both series, compounds were found with excellent contact toxicity to wild-type susceptible (G3) strain and multiply resistant (Akron) strain mosquitoes that carry the G119S resistance mutation of AChE. Compounds possessing good to excellent toxicity to Akron strain mosquitoes inhibit the G119S mutant of An. gambiae AChE (AgAChE) with k(i) values at least 10-to 600-fold higher than that of propoxur, a compound that does not kill Akron mosquitoes at the highest concentration tested. On average, inactivation of WT AgAChE by dimethylcarboxamides 14 was 10-20 fold faster than that of the corresponding isoxazol-3-yl dimethylcarbamates 15. X-ray crystallography of dimethylcarboxamide 14d provided insight into that reactivity, a finding that may explain the inhibitory power of structurally-related inhibitors of hormone-sensitive lipase. Finally, human/An. gambiae AChE inhibition selectivities of these compounds were low, suggesting the need for additional structural modification. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.026
• 作为产物：
  描述：

  2-甲基丁酰氯 在 吡啶 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.75h， 生成 5-sec-butylisoxazol-3-ol
  参考文献：
  名称：

  3-Oxoisoxazole-2(3H)-carboxamides and isoxazol-3-yl carbamates: Resistance-breaking acetylcholinesterase inhibitors targeting the malaria mosquito, Anopheles gambiae

  摘要：

  To identify potential selective and resistance-breaking mosquitocides against the African malaria vector Anopheles gambiae, we investigated the acetylcholinesterase (AChE) inhibitory and mosquitocidal properties of isoxazol-3-yl dimethylcarbamates (15), and the corresponding 3-oxoisoxazole-2(3H)-dimethylcarboxamide isomers (14). In both series, compounds were found with excellent contact toxicity to wild-type susceptible (G3) strain and multiply resistant (Akron) strain mosquitoes that carry the G119S resistance mutation of AChE. Compounds possessing good to excellent toxicity to Akron strain mosquitoes inhibit the G119S mutant of An. gambiae AChE (AgAChE) with k(i) values at least 10-to 600-fold higher than that of propoxur, a compound that does not kill Akron mosquitoes at the highest concentration tested. On average, inactivation of WT AgAChE by dimethylcarboxamides 14 was 10-20 fold faster than that of the corresponding isoxazol-3-yl dimethylcarbamates 15. X-ray crystallography of dimethylcarboxamide 14d provided insight into that reactivity, a finding that may explain the inhibitory power of structurally-related inhibitors of hormone-sensitive lipase. Finally, human/An. gambiae AChE inhibition selectivities of these compounds were low, suggesting the need for additional structural modification. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.026

文献信息

• [EN] HETEROCYCLIC SUBSTITUTED 4-(AMINOMETHYL)-PIPERIDINE BENZAMIDES AS 5HT4-ANTAGONISTS<br/>[FR] 4-(AMINOMETHYL)-PIPERIDINE BENZAMIDES SUBSTITUES PAR DES HETEROCYCLES, UTILISES COMME ANTAGONISTES DES RECEPTEURS 5HT4
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2005003124A1

  公开（公告）日：2005-01-13

  The present invention is concerned with novel compounds of formula (I) having 5HT4-antagonistic properties. The invention further relates to methods for preparing such novel compounds, pharmaceutical compositions comprising said novel compounds as well as the use as a medicine of said compounds.

  本发明涉及具有5HT4拮抗性质的式(I)的新化合物。该发明还涉及制备这种新化合物的方法，包括这些新化合物的药用组合物以及这些化合物作为药物的用途。
• THERAPEUTIC COMPOUNDS
  申请人：Burk Robert M.

  公开号：US20090247594A1

  公开（公告）日：2009-10-01

  Disclosed herein is a compound having a structure or a pharmaceutically acceptable salt thereof, or a prodrug thereof. Therapeutic methods, compositions, and medicaments related thereto are also disclosed.

  本文披露了一种具有以下结构或其药学上可接受的盐或其前药的化合物。还披露了与之相关的治疗方法、组成物和药物。
• Functionalized long-chain hydrocarbon mono- and di-carboxylic acids and their use for the prevention or treatment of disease
  申请人：ESPERVITA THERAPEUTICS, INC.

  公开号：US11084773B1

  公开（公告）日：2021-08-10

  This invention provides compounds of Formulae (IA), (IB), (IC), (ID), (IE), (IF), (IG), (IH), (IJ), (IK), (IL), (II), (III), (IIIA), and (IIIB); pharmaceutically acceptable salts and solvates thereof; and compositions thereof. This invention further provides methods for treating a disease, including but not limited to, liver disease or an abnormal liver condition; cancer (such as hepatocellular carcinoma or cholangiocarcinoma); a malignant or benign tumor of the lung, liver, gall bladder, bile duct or digestive tract; an intra- or extra-hepatic bile duct disease; a disorder of lipoprotein; a lipid-and-metabolic disorder; cirrhosis; fibrosis; a disorder of glucose metabolism; a cardiovascular or related vascular disorder; a disease resulting from steatosis, fibrosis, or cirrhosis; a disease associated with increased inflammation (such as hepatic inflammation or pulmonary inflammation); hepatocyte ballooning; a peroxisome proliferator activated receptor-associated disorder; an ATP citrate lyase disorder; an acetyl-coenzyme A carboxylase disorder; obesity; pancreatitis; or renal disease.

  本发明提供了式(IA)、(IB)、(IC)、(ID)、(IE)、(IF)、(IG)、(IH)、(IJ)、(IK)、(IL)、(II)、(III)、(IIIA)和(IIIB)的化合物；其药学上可接受的盐和溶液；及其组合物。本发明进一步提供了治疗疾病的方法，包括但不限于肝脏疾病或肝脏异常状况；癌症（如肝细胞癌或胆管癌）；肺、肝、胆囊、胆管或消化道的恶性或良性肿瘤；肝内或肝外胆管疾病；脂蛋白紊乱；脂质和代谢紊乱；肝硬化；纤维化；糖代谢紊乱；心血管或相关血管疾病；脂肪变性、纤维化或肝硬化导致的疾病；与炎症（如肝脏炎症或肺部炎症）加重相关的疾病；肝细胞气球化；过氧化物酶体增殖激活受体相关疾病；ATP柠檬酸裂解酶紊乱；乙酰辅酶A羧化酶紊乱；肥胖症；胰腺炎；或肾脏疾病。
• Compounds Useful for Treating Liver Diseases
  申请人：ABIONYX PHARMA SA

  公开号：US20220363632A1

  公开（公告）日：2022-11-17

  This invention provides compounds, for example, of Formulae (A)-(H) and (J)-(AA) and pharmaceutically acceptable salts, solvates, esters, amides, and prodrugs thereof. The invention further provides pharmaceutical compositions comprising a compound of the invention, and a pharmaceutically acceptable carrier or vehicle. The compounds and compositions disclosed herein are useful for treating or preventing various diseases and conditions, for example liver disease such as liver fibrosis, fatty liver disease, non-alcoholic fatty liver disease (NAFLD) or non-alcoholic steatohepatitis (NASH), and kidney diseases such as acute kidney injury (AKI).
• US7732464B2
  申请人：——

  公开号：US7732464B2

  公开（公告）日：2010-06-08