3-(1,3-苯并二恶茂-5-氧基)-1-丙醇 | 247228-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 中文名称: 3-(1,3-苯并二恶茂-5-氧基)-1-丙醇
• 英文名称: 3-(benzo[d][1,3]dioxol-5-yloxy)propan-1-ol
• 英文别名: 3-(1,3-Benzodioxol-5-yloxy)-1-propanol；3-(1,3-benzodioxol-5-yloxy)propan-1-ol
• CAS: 247228-25-7
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: DETIXCLFDUOEGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  314℃
• 密度：
  1.264
• 闪点：
  144℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(1,3-苯并二恶茂-5-氧基)-1-丙醇 在 lithium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 27.0h， 生成 1-[3-(3,4-亚甲基二氧基苯氧基)丙基]-4-苯基哌嗪马来酸盐
  参考文献：
  名称：

  Discovery of LASSBio-772, a 1,3-benzodioxole N-phenylpiperazine derivative with potent alpha 1A/D-Adrenergic receptor blocking properties

  摘要：

  We described herein the discovery of 1-(2-(benzo[d] [1,3]dioxol-6-yl)ethyl)-4-(2-methoxyphenyl) piperazine (LASSBio-772), as a novel potent and selective alpha 1A/1D adrenoceptor (AR) antagonist selected after screening of functionalized N-phenylpiperazine derivatives in phenylephrine-induced vasoconstriction of rabbit aorta rings. The affinity of LASSBio-772 for alpha 1A and alpha 1B AR subtypes was determined through displacement of [(3)H]prazosin binding. We obtained Ki values of 0.14 nM for the alpha 1A-AR, similar to that displayed by tamsulosin (K(i) = 0.13 nM) and 5.55 nM for the alpha 1B-AR, representing a 40-fold higher affinity for alpha 1A-AR. LASSBio-772 also presented high affinity (K(B) = 0.025 nM) for the alpha 1D-AR subtype in the functional rat aorta assay, showing to be equipotent to tamsulosin (K(B) = 0.017 nM). (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.032
• 作为产物：
  描述：

  芝麻酚 在 dimethyl sulfide borane 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 52.0h， 生成 3-(1,3-苯并二恶茂-5-氧基)-1-丙醇
  参考文献：
  名称：

  Discovery of LASSBio-772, a 1,3-benzodioxole N-phenylpiperazine derivative with potent alpha 1A/D-Adrenergic receptor blocking properties

  摘要：

  We described herein the discovery of 1-(2-(benzo[d] [1,3]dioxol-6-yl)ethyl)-4-(2-methoxyphenyl) piperazine (LASSBio-772), as a novel potent and selective alpha 1A/1D adrenoceptor (AR) antagonist selected after screening of functionalized N-phenylpiperazine derivatives in phenylephrine-induced vasoconstriction of rabbit aorta rings. The affinity of LASSBio-772 for alpha 1A and alpha 1B AR subtypes was determined through displacement of [(3)H]prazosin binding. We obtained Ki values of 0.14 nM for the alpha 1A-AR, similar to that displayed by tamsulosin (K(i) = 0.13 nM) and 5.55 nM for the alpha 1B-AR, representing a 40-fold higher affinity for alpha 1A-AR. LASSBio-772 also presented high affinity (K(B) = 0.025 nM) for the alpha 1D-AR subtype in the functional rat aorta assay, showing to be equipotent to tamsulosin (K(B) = 0.017 nM). (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.032

文献信息

• COMPOUNDS AND METHODS OF USE
  申请人：Baell Jonathan Bayldon

  公开号：US20100190782A1

  公开（公告）日：2010-07-29

  In one aspect, the present invention provides for a compound of Formula I in which in Formula I, the variables X 1 , X 2a , X 2b , X 2c , R 1 , B, L, E, A and the subscript n are as defined herein. In another aspect, the present invention provides for pharmaceutical compositions comprising compounds of Formula I as well as methods for using compounds of Formula I for the treatment of diseases and conditions (e.g., cancer, thrombocythemia, etc) characterized by the expression or over-expression of Bcl-2 anti-apoptotic proteins, e.g., of anti-apoptotic Bcl-x L proteins.

  在一个方面，本发明提供了一种I式化合物，其中在I式中，变量X1、X2a、X2b、X2c、R1、B、L、E、A和下标n的定义如本文所述。在另一个方面，本发明提供了包括I式化合物的制药组合物，以及使用I式化合物治疗疾病和病情（如癌症、血小板增多症等）的方法，其中这些疾病和病情的特征是Bcl-2抗凋亡蛋白的表达或过度表达，例如抗凋亡Bcl-xL蛋白。
• US8114893B2
  申请人：——

  公开号：US8114893B2

  公开（公告）日：2012-02-14
• US8518970B2
  申请人：——

  公开号：US8518970B2

  公开（公告）日：2013-08-27
• US9067928B2
  申请人：——

  公开号：US9067928B2

  公开（公告）日：2015-06-30
• Discovery of LASSBio-772, a 1,3-benzodioxole N-phenylpiperazine derivative with potent alpha 1A/D-Adrenergic receptor blocking properties
  作者：Luiz A.S. Romeiro、Marcos da Silva Ferreira、Leandro L. da Silva、Helena C. Castro、Ana L.P. Miranda、Cláudia L.M. Silva、François Noël、Jéssica B. Nascimento、Claudia V. Araújo、Eduardo Tibiriçá、Eliezer J. Barreiro、Carlos A.M. Fraga

  DOI：10.1016/j.ejmech.2011.04.032

  日期：2011.7

  We described herein the discovery of 1-(2-(benzo[d] [1,3]dioxol-6-yl)ethyl)-4-(2-methoxyphenyl) piperazine (LASSBio-772), as a novel potent and selective alpha 1A/1D adrenoceptor (AR) antagonist selected after screening of functionalized N-phenylpiperazine derivatives in phenylephrine-induced vasoconstriction of rabbit aorta rings. The affinity of LASSBio-772 for alpha 1A and alpha 1B AR subtypes was determined through displacement of [(3)H]prazosin binding. We obtained Ki values of 0.14 nM for the alpha 1A-AR, similar to that displayed by tamsulosin (K(i) = 0.13 nM) and 5.55 nM for the alpha 1B-AR, representing a 40-fold higher affinity for alpha 1A-AR. LASSBio-772 also presented high affinity (K(B) = 0.025 nM) for the alpha 1D-AR subtype in the functional rat aorta assay, showing to be equipotent to tamsulosin (K(B) = 0.017 nM). (C) 2011 Elsevier Masson SAS. All rights reserved.