(R)-1-[4-(Benzo[1,3]dioxole-5-sulfonyl)-phenyl]-ethanol | 203180-23-8

• 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: (R)-1-[4-(Benzo[1,3]dioxole-5-sulfonyl)-phenyl]-ethanol
• 英文别名: (1R)-1-[4-(1,3-benzodioxol-5-ylsulfonyl)phenyl]ethanol
• CAS: 203180-23-8
• 化学式: C₁₅H₁₄O₅S
• 分子量: 306.339
• InChiKey: UZUASRNRCUDKJP-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-1-[4-(Benzo[1,3]dioxole-5-sulfonyl)-phenyl]-ethanol 在 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Piperazine-Based CCR5 antagonists as HIV-1 inhibitors. I: 2(S)-methyl piperazine as a key pharmacophore element

  摘要：

  Optimization of the piperidino-piperazines 1 and 2 provided early leads 3 and 4, which showed good activity in the CCR5-RANTES binding assay and in antiviral assays. A systematic study around these structures showed that the 2(S)-methyl piperazine is essential for CCR5 affinity, which is further enhanced by forming the 2,6-dimethyl benzamide of the piperidine. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00381-x
• 作为产物：
  描述：

  1-碘-3,4-亚甲基二氧基苯 在 copper(l) iodide 、 dimethyl sulfide borane 、 碳酸氢钠 、 potassium carbonate 、 间氯过氧苯甲酸 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 (R)-1-[4-(Benzo[1,3]dioxole-5-sulfonyl)-phenyl]-ethanol
  参考文献：
  名称：

  Substituted 2-(R)-Methyl piperazines as muscarinic M2 selective ligands

  摘要：

  A novel series of 2-(R)-methyl-substituted piperazines (e.g.. 2) is described. They are potent M-2 selective ligands that have > 100-fold selectivity versus the M-1 receptor. In the rat microdialysis assay. compound 14 showed significantly enhanced levels of acetylcholine after oral administration. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00023-9

文献信息

• Piperazine derivatives useful as CCR5 antagonists
  申请人：Schering Corporation

  公开号：US06391865B1

  公开（公告）日：2002-05-21

  The use of CCR5 antagonists of the formula or a pharmaceutically acceptable salt thereof, wherein R is optionally substituted phenyl, pyridyl, thiophenyl or naphthyl; R1 is hydrogen or alkyl; R2 is substituted phenyl, substituted heteroaryl, naphthyl, fluorenyl, diphenylmethyl or optionally substituted phenyl- or heteroaryl-alkyl; R3 is hydrogen, alkyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, or optionally substituted phenyl, phenylalkyl, naphthyl, naphthylalkyl, heteroaryl or heteroarylalkyl; R4, R5 and R7 are hydrogen or alkyl; R6 is hydrogen, alkyl or alkenyl; for the treatment of HIV, solid organ transplant rejection, graft v. host disease, arthritis, rheumatoid arthritis, inflammatory bowel disease, atopic dermatitis, psoriasis, asthma, allergies or multiple sclerosis is disclosed, as well as novel compounds, pharmaceutical compositions comprising them, and the combination of CCR5 antagonists of the invention in combination with antiviral agents useful in the treatment of HIV or agents useful in the treatment of inflammatory diseases.

  公开了使用CCR5拮抗剂的公式，其中 R是可选择的取代苯基，吡啶基，噻吩基或萘基; R1是氢或烷基; R2是取代苯基，取代杂环基，萘基，芴基，二苯甲基或可选择的取代苯基或杂环基烷基; R3是氢，烷基，烷氧基烷基，环烷基，环烷基烷基，或可选择的取代苯基，苯基烷基，萘基，萘基烷基，杂环基或杂环基烷基; R4，R5和R7是氢或烷基; R6是氢，烷基或烯基; 用于治疗HIV，固体器官移植排斥，移植物宿主病，关节炎，类风湿关节炎，炎症性肠病，特应性皮炎，牛皮癣，哮喘，过敏或多发性硬化症的方法，以及包含它们的新化合物，包含它们的药物组合物，以及CCR5拮抗剂与抗HIV治疗中有用的抗病毒剂或与治疗炎症性疾病中有用的药物的组合。