3-氯-5-丙氧基苯基硼酸 | 1256345-74-0

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-氯-5-丙氧基苯基硼酸
• 中文别名: 3-氯-5-丙氧基苯硼酸
• 英文名称: (3-chloro-5-propoxyphenyl)boronic acid
• CAS: 1256345-74-0
• 化学式: C₉H₁₂BClO₃
• 分子量: 214.456
• InChiKey: SPWXUQOZAXXFGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.81
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  N-{4-[1-(5-(6-methoxy-2-naphthyl)-3-{[(trifluoromethyl)sulfonyl]oxy}-1H-pyrazol-1-yl)ethyl]benzoyl}-β-alaninate 、 3-氯-5-丙氧基苯基硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Discovery of a Novel Glucagon Receptor Antagonist N-[(4-{(1S)-1-[3-(3, 5-Dichlorophenyl)-5-(6-methoxynaphthalen-2-yl)-1H-pyrazol-1-yl]ethyl}phenyl)carbonyl]-β-alanine (MK-0893) for the Treatment of Type II Diabetes

  摘要：

  A potent, selective glucagon receptor antagonist 9m, N-[(4-{(1S)-1-[3-(3,5-dichlorophenyl) -5-(6-methoxynaphthalen-2-yl)-1H-pyrazol-1-yl]ethyl}phenyl)-carbonyl]-beta-alanine, was discovered by optimization of a previously identified lead. Compound 9m is a reversible and competitive antagonist with high binding affinity (IC50 of 6.6 nM) and functional cAMP activity (IC50 of 15.7 nM). It is selective for glucagon receptor relative to other family B GPCRs, showing IC50 values of 1020 nM for GIPR, 9200 nM for PAC1, and >10000 nM for GLP-1R, VPAC1, and VPAC2. Compound 9m blunted glucagon-induced glucose elevation in hGCGR mice and rhesus monkeys. It also lowered ambient glucose levels in both acute and chronic mouse models: in hGCGR ob/ob mice it reduced glucose (AUC 0-6 h) by 32% and 39% at 3 and 10 mpk single doses, respectively. In hGCGR mice on a high fat diet, compound 9m at 3, and 10 mpk po in feed lowered blood glucose levels by 89% and 94% at day 10, respectively, relative to the difference between the vehicle control and lean hGCGR mice. On the basis of its favorable biological and DMPK properties, compound 9m (MK-0893) was selected for further preclinical and clinical evaluations.

  DOI：

  10.1021/jm300579z

文献信息

• [EN] NON-COVALENT INHIBITORS OF THE MAIN PROTEASE OF SARS-COV-2 AND METHODS OF USE<br/>[FR] INHIBITEURS NON COVALENTS DE LA PROTÉASE PRINCIPALE DU SRAS-COV-2 ET PROCÉDÉS D'UTILISATION
  申请人：UNIV YALE

  公开号：WO2022150584A1

  公开（公告）日：2022-07-14

  Provided herein are compounds of formula (I) or (I-A), which act as non-covalent inhibitors of SARS-CoV2 main protease (Mpro). The compounds of formula (I) or (I-A) are useful in treating COVID-19 infections, as well as reducing or ameliorating symptoms associated with COVID-19 infection.

  本文提供了化合物(I)或(I-A)的公式，它们作为SARS-CoV2主要蛋白酶(Mpro)的非共价抑制剂。化合物(I)或(I-A)的公式在治疗COVID-19感染以及减少或缓解与COVID-19感染相关的症状方面非常有用。
• Optimization of Triarylpyridinone Inhibitors of the Main Protease of SARS-CoV-2 to Low-Nanomolar Antiviral Potency
  作者：Chun-Hui Zhang、Krasimir A. Spasov、Raquel A. Reilly、Klarissa Hollander、Elizabeth A. Stone、Joseph A. Ippolito、Maria-Elena Liosi、Maya G. Deshmukh、Julian Tirado-Rives、Shuo Zhang、Zhuobin Liang、Scott J. Miller、Farren Isaacs、Brett D. Lindenbach、Karen S. Anderson、William L. Jorgensen

  DOI：10.1021/acsmedchemlett.1c00326

  日期：2021.8.12
• [EN] NON-COVALENT INHIBITORS OF THE MAIN PROTEASE OF SARS-COV-2 AND METHODS OF USE<br/>[FR] INHIBITEURS NON COVALENTS DE LA PROTÉASE PRINCIPALE DU SARS-COV-2 ET PROCÉDÉS D'UTILISATION
  申请人：[en]YALE UNIVERSITY

  公开号：WO2024010585A1

  公开（公告）日：2024-01-11

  Provided herein are compounds of formula (I) or (I-A), which act as non-covalent inhibitors of SARS-CoV2 main protease (Mpro). The compounds of formula (I) or (I-A) are useful in treating, ameliorating, and/or preventing COVID-19 infections, as well as reducing or ameliorating symptoms associated with COVID-19 infection.
• Discovery of a Novel Glucagon Receptor Antagonist <i>N</i>-[(4-{(1<i>S</i>)-1-[3-(3, 5-Dichlorophenyl)-5-(6-methoxynaphthalen-2-yl)-1<i>H</i>-pyrazol-1-yl]ethyl}phenyl)carbonyl]-β-alanine (MK-0893) for the Treatment of Type II Diabetes
  作者：Yusheng Xiong、Jian Guo、Mari R. Candelore、Rui Liang、Corey Miller、Qing Dallas-Yang、Guoqiang Jiang、Peggy E. McCann、Sajjad A. Qureshi、Xinchun Tong、Shiyao Sherrie Xu、Jackie Shang、Stella H. Vincent、Laurie M. Tota、Michael J. Wright、Xiaodong Yang、Bei B. Zhang、James R. Tata、Emma R. Parmee

  DOI：10.1021/jm300579z

  日期：2012.7.12

  A potent, selective glucagon receptor antagonist 9m, N-[(4-(1S)-1-[3-(3,5-dichlorophenyl) -5-(6-methoxynaphthalen-2-yl)-1H-pyrazol-1-yl]ethyl}phenyl)-carbonyl]-beta-alanine, was discovered by optimization of a previously identified lead. Compound 9m is a reversible and competitive antagonist with high binding affinity (IC50 of 6.6 nM) and functional cAMP activity (IC50 of 15.7 nM). It is selective for glucagon receptor relative to other family B GPCRs, showing IC50 values of 1020 nM for GIPR, 9200 nM for PAC1, and >10000 nM for GLP-1R, VPAC1, and VPAC2. Compound 9m blunted glucagon-induced glucose elevation in hGCGR mice and rhesus monkeys. It also lowered ambient glucose levels in both acute and chronic mouse models: in hGCGR ob/ob mice it reduced glucose (AUC 0-6 h) by 32% and 39% at 3 and 10 mpk single doses, respectively. In hGCGR mice on a high fat diet, compound 9m at 3, and 10 mpk po in feed lowered blood glucose levels by 89% and 94% at day 10, respectively, relative to the difference between the vehicle control and lean hGCGR mice. On the basis of its favorable biological and DMPK properties, compound 9m (MK-0893) was selected for further preclinical and clinical evaluations.