(E)-4-bromo-2-(3-methyl-4-(prop-2-ynyloxy)but-2-enyl)phenol | 1379810-84-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-4-bromo-2-(3-methyl-4-(prop-2-ynyloxy)but-2-enyl)phenol
• 英文别名: 4-bromo-2-[(E)-3-methyl-4-prop-2-ynoxybut-2-enyl]phenol
• CAS: 1379810-84-0
• 化学式: C₁₄H₁₅BrO₂
• 分子量: 295.176
• InChiKey: ZGULEIMVXALYSL-NYYWCZLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-bromo-2-(3-methyl-4-(prop-2-ynyloxy)but-2-enyl)phenol 在 三苯基膦双(三氟甲磺酰亚胺)金 、 臭氧 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 70.0h， 生成 (4aR,10aR)-7-bromo-10a-methyl-1,4a,5,10a-tetrahydropyrano[3,4-b]chromen-4(3H)-one
  参考文献：
  名称：

  Synthesis, characterization, and PK/PD studies of a series of spirocyclic pyranochromene BACE1 inhibitors

  摘要：

  The development of 1,3,4,4a,5,10a-hexahydropyrano[3,4-b]chromene analogs as BACE1 inhibitors is described. Introduction of the spirocyclic pyranochromene scaffold yielded several advantages over previous generation cores, including increased potency, reduced efflux, and reduced CYP2D6 inhibition. Compound 13 ( BACE1 IC50 = 110 nM) demonstrated a reduction in CSF Ab in wild type rats after a single dose. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.012
• 作为产物：
  描述：

  一氧化异戊二烯 在 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 四氯化钛 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 、 甲苯 、 mineral oil 为溶剂， 反应 31.83h， 生成 (E)-4-bromo-2-(3-methyl-4-(prop-2-ynyloxy)but-2-enyl)phenol
  参考文献：
  名称：

  Synthesis, characterization, and PK/PD studies of a series of spirocyclic pyranochromene BACE1 inhibitors

  摘要：

  The development of 1,3,4,4a,5,10a-hexahydropyrano[3,4-b]chromene analogs as BACE1 inhibitors is described. Introduction of the spirocyclic pyranochromene scaffold yielded several advantages over previous generation cores, including increased potency, reduced efflux, and reduced CYP2D6 inhibition. Compound 13 ( BACE1 IC50 = 110 nM) demonstrated a reduction in CSF Ab in wild type rats after a single dose. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.012

文献信息

• [EN] HETEROCYCLIC INHIBITORS OF BETA - SECRETASE FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES<br/>[FR] INHIBITEURS HÉTÉROCYCLIQUES DE LA BÊTA-SECRÉTASE POUR LE TRAITEMENT DE MALADIES NEURODÉGÉNÉRATIVES
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2012071458A1

  公开（公告）日：2012-05-31

  The invention provides novel tricyclic compounds of Formula I' that inhibit β-secretase cleavage of APP and are useful as therapeutic agents for treating neurodegenerative diseases.

  本发明提供了一种抑制β-分泌酶裂解APP的新颖三环化合物，式I'，可用作治疗神经退行性疾病的治疗剂。
• COMPOUNDS FOR TREATING NEURODEGENERATIVE DISEASES
  申请人：Cook Adam

  公开号：US20120157448A1

  公开（公告）日：2012-06-21

  The invention provides novel tricyclic compounds of Formula I′ that inhibit β-secretase cleavage of APP and are useful as therapeutic agents for treating neurodegenerative diseases.

  该发明提供了一种新型三环化合物I'的公式，它能够抑制β-分泌酶对APP的剪切，并且可用作治疗神经退行性疾病的治疗剂。
• Synthesis, characterization, and PK/PD studies of a series of spirocyclic pyranochromene BACE1 inhibitors
  作者：Matthew Volgraf、Lina Chan、Malcolm P. Huestis、Hans E. Purkey、Michael Burkard、Mary Geck Do、Julie Harris、Kevin W. Hunt、Xingrong Liu、Joseph P. Lyssikatos、Sumeet Rana、Allen A. Thomas、Guy P.A. Vigers、Michael Siu

  DOI：10.1016/j.bmcl.2014.04.012

  日期：2014.6

  The development of 1,3,4,4a,5,10a-hexahydropyrano[3,4-b]chromene analogs as BACE1 inhibitors is described. Introduction of the spirocyclic pyranochromene scaffold yielded several advantages over previous generation cores, including increased potency, reduced efflux, and reduced CYP2D6 inhibition. Compound 13 ( BACE1 IC50 = 110 nM) demonstrated a reduction in CSF Ab in wild type rats after a single dose. (C) 2014 Elsevier Ltd. All rights reserved.