(6-isopropyl-2-naphthyl)boronic acid | 878200-80-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (6-isopropyl-2-naphthyl)boronic acid
• 英文别名: 6-Isopropylnaphthalene-2-boronic acid；(6-propan-2-ylnaphthalen-2-yl)boronic acid
• CAS: 878200-80-7
• 化学式: C₁₃H₁₅BO₂
• 分子量: 214.072
• InChiKey: LRZBGTLQWWMLID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6-isopropyl-2-naphthyl)boronic acid 、 tert-butyl N-{4-[1-(3-(3,5-dichlorophenyl)-5-{[(trifluoromethyl)sulfonyl]oxy}-1H-pyrazol-1-yl)ethyl]-benzoyl}-β-alaninate 在 四(三苯基膦)钯 、 三乙胺 、 三氟乙酸 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 N-({4-[(1S)-1-{3-(3,5-dichlorophenyl)-5-[6-(propan-2-yl)naphthalen-2-yl]-1H-pyrazol-1-yl}ethyl]phenyl}carbonyl)-β-alanine
  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
• 作为产物：
  描述：

  (6-isopropenyl-2-naphthyl)boronic acid 在 钯 氢气 、 crude product 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (6-isopropyl-2-naphthyl)boronic acid
  参考文献：
  名称：

  Pyrazole derivatives, compositions containing such compounds and methods of use

  摘要：

  本文披露了附有萘基团的吡唑类化合物。这些化合物可用于治疗2型糖尿病及相关疾病。此外，还包括制药组合物和治疗方法。

  公开号：

  US20070088070A1

文献信息

• Aromatic amine derivative and organic electroluminescence device employing the same
  申请人：Funahashi Masakazu

  公开号：US20060152146A1

  公开（公告）日：2006-07-13

  A specified aromatic amine derivative having a chrysene structure. An organic electroluminescence device which comprises at least one organic thin film layer comprising a light emitting layer sandwiched between a pair of electrode consisting of an anode and a cathode, wherein at least one of the organic thin film layer comprises the aromatic amine derivative singly or as its mixture component. Organic electroluminescence devices having a long lifetime and a high efficiency of light emission, and aromatic amine derivatives capable of realizing such organic electroluminescence devices are provided.

  提供一种具有蒽结构的特定芳香胺衍生物。一种有机电致发光器件，其包括至少一个有机薄膜层，该有机薄膜层包括夹在由阳极和阴极组成的一对电极之间的发光层，其中至少一个有机薄膜层包含该芳香胺衍生物单独或作为其混合组分。提供具有长寿命和高发光效率的有机电致发光器件以及能够实现这种有机电致发光器件的芳香胺衍生物。
• AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENCE DEVICE EMPLOYING THE SAME
  申请人：Funahashi Masakazu

  公开号：US20080268283A1

  公开（公告）日：2008-10-30

  A specified aromatic amine derivative having a chrysene structure. An organic electroluminescence device which comprises at least one organic thin film layer comprising a light emitting layer sandwiched between a pair of electrode consisting of an anode and a cathode, wherein at least one of the organic thin film layer comprises the aromatic amine derivative singly or as its mixture component. Organic electroluminescence devices having a long lifetime and a high efficiency of light emission, and aromatic amine derivatives capable of realizing such organic electroluminescence devices are provided.

  提供一种具有蒽结构的指定芳香胺衍生物。一种有机电致发光装置，其包括至少一个有机薄膜层，其中包括一个发光层，夹在由阳极和阴极组成的一对电极之间，其中至少一个有机薄膜层单独或作为其混合组分包含芳香胺衍生物。提供具有长寿命和高发光效率的有机电致发光装置以及能够实现这种有机电致发光装置的芳香胺衍生物。
• Pyrazole derivatives, compositions containing such compounds and methods of use
  申请人：Parmee R. Emma

  公开号：US20070088070A1

  公开（公告）日：2007-04-19

  Pyrazoles having a naphthyl group attached are disclosed. The compounds are useful for treating type 2 diabetes and related conditions. Pharmaceutical compositions and methods of treatment are also included.

  含有萘基团的吡唑类化合物已被披露。这些化合物对治疗2型糖尿病及相关疾病有用。同时还包括了药物组合物和治疗方法。
• 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.