2-(3-Methyl-isothiazol-5-yl)-phenol | 120869-49-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(3-Methyl-isothiazol-5-yl)-phenol
• 英文别名: 2-(3-Methyl-5-isothiazolyl)phenol；2-(3-methyl-1,2-thiazol-5-yl)phenol
• CAS: 120869-49-0
• 化学式: C₁₀H₉NOS
• 分子量: 191.254
• InChiKey: KJDUPMQXPHTGPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-Methyl-isothiazol-5-yl)-phenol 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 5-[2-(4,5-dihydro-1H-imidazol-2-ylmethoxy)-phenyl]-3-methyl-isothiazole
  参考文献：
  名称：

  α1-Adrenoceptor Agonists: The Identification of Novel α1A Subtype Selective 2′-Heteroaryl-2-(phenoxymethyl)imidazolines

  摘要：

  Novel 2'-heteroaryl-2-(phenoxymethyl)imidazolines have been identified as potent agonists of the cloned human alpha(1)-adrenoceptors in vitro. The nature of the 2'-heteroaryl group can have significant effects on the potency, efficacy, and subtype selectivity in this series. alpha(1A) Subtype selective agonists have been identified. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00764-8
• 作为产物：
  描述：

  2-methylbenzopyran-4-thione 在 S,S-二苯基硫亚胺 作用下， 以 氯仿 为溶剂， 生成 2-(3-Methyl-isothiazol-5-yl)-phenol
  参考文献：
  名称：

  α1-Adrenoceptor Agonists: The Identification of Novel α1A Subtype Selective 2′-Heteroaryl-2-(phenoxymethyl)imidazolines

  摘要：

  Novel 2'-heteroaryl-2-(phenoxymethyl)imidazolines have been identified as potent agonists of the cloned human alpha(1)-adrenoceptors in vitro. The nature of the 2'-heteroaryl group can have significant effects on the potency, efficacy, and subtype selectivity in this series. alpha(1A) Subtype selective agonists have been identified. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00764-8

文献信息

• Design of Pyridopyrazine-1,6-dione γ-Secretase Modulators that Align Potency, MDR Efflux Ratio, and Metabolic Stability
  作者：Martin Pettersson、Douglas S. Johnson、John M. Humphrey、Todd W. Butler、Christopher W. am Ende、Benjamin A. Fish、Michael E. Green、Gregory W. Kauffman、Patrick B. Mullins、Christopher J. O’Donnell、Antonia F. Stepan、Cory M. Stiff、Chakrapani Subramanyam、Tuan P. Tran、Beth Cooper Vetelino、Eddie Yang、Longfei Xie、Kelly R. Bales、Leslie R. Pustilnik、Stefanus J. Steyn、Kathleen M. Wood、Patrick R. Verhoest

  DOI：10.1021/acsmedchemlett.5b00070

  日期：2015.5.14

  Herein we describe the design and synthesis of a series of pyridopyrazine-1,6-dione gamma-secretase modulators (GSMs) for Alzheimer's disease (AD) that achieve good alignment of potency, metabolic stability, and low MDR efflux ratios, while also maintaining favorable physicochemical properties. Specifically, incorporation of fluorine enabled design of metabolically less liable lipophilic alkyl substituents to increase potency without compromising the sp(3)-character. The lead compound 21 (PF-06442609) displayed a favorable rodent pharmacokinetic profile, and robust reductions of brain A beta 42 and A beta 40 were observed in a guinea pig time-course experiment.
• Buggle, Katherine; Fallon, Bernadette, Journal of Chemical Research, Miniprint, 1988, # 11, p. 2764 - 2784
  作者：Buggle, Katherine、Fallon, Bernadette

  DOI：——

  日期：——
• BUGGLE, KATHERINE;FALLON, BERNADETTE
  作者：BUGGLE, KATHERINE、FALLON, BERNADETTE

  DOI：——

  日期：——
• α1-Adrenoceptor Agonists: The Identification of Novel α1A Subtype Selective 2′-Heteroaryl-2-(phenoxymethyl)imidazolines
  作者：Michael J Bishop、Kevin A Barvian、Judd Berman、Eric C Bigham、Deanna T Garrison、Michael J Gobel、Stephen J Hodson、Paul E Irving、James A Liacos、Frank Navas, III、David L Saussy、Jason D Speake

  DOI：10.1016/s0960-894x(01)00764-8

  日期：2002.2

  Novel 2'-heteroaryl-2-(phenoxymethyl)imidazolines have been identified as potent agonists of the cloned human alpha(1)-adrenoceptors in vitro. The nature of the 2'-heteroaryl group can have significant effects on the potency, efficacy, and subtype selectivity in this series. alpha(1A) Subtype selective agonists have been identified. (C) 2002 Elsevier Science Ltd. All rights reserved.