4-(benzo[d][1,3]dioxol-5-yl)butyl methanesulfonate

• 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
• 英文名称: 4-(benzo[d][1,3]dioxol-5-yl)butyl methanesulfonate
• 英文别名: 4-(3,4-methylenedioxyphenyl-1-yl)butane-1-yl mesylate；4-(1,3-Benzodioxol-5-yl)butyl methanesulfonate
• 化学式: C₁₂H₁₆O₅S
• 分子量: 272.322
• InChiKey: LCABBZCLDZXZEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-苯基哌嗪 、 4-(benzo[d][1,3]dioxol-5-yl)butyl methanesulfonate 在 lithium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以93%的产率得到1-(4-(benzo[d] [1,3]dioxol-5-yl)butyl)-4-phenylpiperazine
  参考文献：
  名称：

  Use of Adrenergic N-Phenylpiperazine Antagonists, Pahrmaceutical Compositions Containning Them, and Methods of Preparing Them

  摘要：

  本发明描述了与公式（I）相对应的苯基哌嗪基α肾上腺素受体拮抗剂，其选择性作用于α1A/α1D亚型，其中与α1B亚型相比的选择性指数，对于α1A亚型至少为1700，对于α1D亚型至少为10000，因此可用于治疗哺乳动物，尤其是人类的下尿路症状，包括良性前列腺增生的治疗。还描述了含有该化合物的药物组合物以及其制备方法。

  公开号：

  US20070219213A1
• 作为产物：
  描述：

  黄樟素 在 盐酸 、 lithium aluminium tetrahydride 、 dimethyl sulfide borane 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 65.33h， 生成 4-(benzo[d][1,3]dioxol-5-yl)butyl methanesulfonate
  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

• Use of Adrenergic N-Phenylpiperazine Antagonists, Pahrmaceutical Compositions Containning Them, and Methods of Preparing Them
  申请人：Soares Romeiro Antonio Luiz

  公开号：US20070219213A1

  公开（公告）日：2007-09-20

  The present invention describes phenylpiperazinyl alpha adrenergic antagonists that corresponds to the formula (I) which selectively act on the alpha 1A/alpha 1D subtypes, where its selectivity index in comparison to alpha 1B subtype is, at minimum, 1700 for the alpha 1A subtype and 10000 for the alpha 1 D subtype, being therefore useful for the treatment of the lower urinary tract symptoms, including the benign prostatic hyperplasia treatment in mammals, preferentially humans. It is also described pharmaceutical compositions containing said compounds and methods for its preparation.

  本发明描述了与公式（I）相对应的苯基哌嗪基α肾上腺素受体拮抗剂，其选择性作用于α1A/α1D亚型，其中与α1B亚型相比的选择性指数，对于α1A亚型至少为1700，对于α1D亚型至少为10000，因此可用于治疗哺乳动物，尤其是人类的下尿路症状，包括良性前列腺增生的治疗。还描述了含有该化合物的药物组合物以及其制备方法。
• 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.