4-[2-(4-benzoyl-2(R)-methylpiperazin-1-yl)-2-oxoacetyl]phenylboronic acid | 948990-79-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[2-(4-benzoyl-2(R)-methylpiperazin-1-yl)-2-oxoacetyl]phenylboronic acid
• 英文别名: 4-[2-((R)-4-benzoyl-2-methyl-piperazin-1-yl)-2-oxo-acetyl]-boronic acid；[4-[2-[(2R)-4-benzoyl-2-methylpiperazin-1-yl]-2-oxoacetyl]phenyl]boronic acid
• CAS: 948990-79-2
• 化学式: C₂₀H₂₁BN₂O₅
• 分子量: 380.208
• InChiKey: UCZPWXPHNPNLAM-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.08
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  98.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  四氢吡咯 、 4-[2-(4-benzoyl-2(R)-methylpiperazin-1-yl)-2-oxoacetyl]phenylboronic acid 在 copper diacetate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以56%的产率得到1-((R)-4-benzoyl-2-methylpiperazin-1-yl)-2-(4-pyrrolidin-1-ylphenyl)ethane-1,2-dione
  参考文献：
  名称：

  Heterobiaryl Human Immunodeficiency Virus Entry Inhibitors

  摘要：

  Previously disclosed HIV (human immunodeficiency virus) attachment inhibitors, exemplified by BMS 806 (formally BMS378806, 1), are characterized by a substituted indole or azaindole ring linked to a benzoylpiperazine via a ketoamide or sulfonamide group. In the present report, we describe the discovery of a novel series of potent HIV entry inhibitors in which the indole or azaindole ring of previous inhibitors is replaced by a heterobiaryl group. Several of these analogues exhibited IC(50) values of less than 5 nM in a pseudotyped antiviral assay, and compound 13k was demonstrated to exhibit potency and selectivity similar to those of I against a panel of clinical viral isolates. Moreover, current structure-activity relationship studies of these novel biaryl gp120 inhibitors revealed that around the biaryl, a fine crevice might exist in the gp120 binding site. Taken in sum, these data reveal a hitherto unsuspected flexibility in the structure-activity relationships for these inhibitors and suggest new avenues for exploration and gp120 inhibitor design.

  DOI：

  10.1021/jm900330x
• 作为产物：
  描述：

  1-((R)-4-benzoyl-2-methylpiperazin-1-yl)-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]ethane-1,2-dione 在 sodium periodate 、 ammonium acetate 、 水 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 4-[2-(4-benzoyl-2(R)-methylpiperazin-1-yl)-2-oxoacetyl]phenylboronic acid
  参考文献：
  名称：

  WO2007/103456

  摘要：

  公开号：