2-methyl-2-(1H-tetraazol-5-yl)propanoic acid | 716358-44-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methyl-2-(1H-tetraazol-5-yl)propanoic acid
• 英文别名: 2-Methyl-2-(1h-1,2,3,4-tetrazol-5-yl)propanoic acid；2-methyl-2-(2H-tetrazol-5-yl)propanoic acid
• CAS: 716358-44-0
• 化学式: C₅H₈N₄O₂
• 分子量: 156.144
• InChiKey: MINPAAYUJLDDTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  、 2-methyl-2-(1H-tetraazol-5-yl)propanoic acid 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Novel 4,4-Disubstituted Piperidine-Based C–C Chemokine Receptor-5 Inhibitors with High Potency against Human Immunodeficiency Virus-1 and an Improved human Ether-a-go-go Related Gene (hERG) Profile

  摘要：

  We recently described (J. Med. Chem. 2008, 51, 6538-6546) a novel class of CCR5 antagonists with strong anti-HIV potency. Herein, we detail SAR converting leads 1 and 2 to druglike molecules. The pivotal structural motif enabling this transition was the secondary sulfonamide substituent. Further fine-tuning of the substituent pattern in the sulfonamide paved the way to enhancing potency and bioavailability and minimizing hERG inhibition, resulting in discovery of clinical compound 122 (GSK163929).

  DOI：

  10.1021/jm200279v
• 作为产物：
  描述：

  2-氰基-2-甲基丙酸乙酯 在 叠氮基三甲基硅烷 、 二正丁基氧化锡 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 生成 2-methyl-2-(1H-tetraazol-5-yl)propanoic acid
  参考文献：
  名称：

  Novel 4,4-Disubstituted Piperidine-Based C–C Chemokine Receptor-5 Inhibitors with High Potency against Human Immunodeficiency Virus-1 and an Improved human Ether-a-go-go Related Gene (hERG) Profile

  摘要：

  We recently described (J. Med. Chem. 2008, 51, 6538-6546) a novel class of CCR5 antagonists with strong anti-HIV potency. Herein, we detail SAR converting leads 1 and 2 to druglike molecules. The pivotal structural motif enabling this transition was the secondary sulfonamide substituent. Further fine-tuning of the substituent pattern in the sulfonamide paved the way to enhancing potency and bioavailability and minimizing hERG inhibition, resulting in discovery of clinical compound 122 (GSK163929).

  DOI：

  10.1021/jm200279v

文献信息

• [EN] PIPERIDINE DERIVATIVES AS CCR5 ANTAGONISTS<br/>[FR] ANTAGONISTES DE CCR5 UTILES COMME AGENTS THERAPEUTIQUES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2004054974A3

  公开（公告）日：2004-09-02
• Novel 4,4-Disubstituted Piperidine-Based C–C Chemokine Receptor-5 Inhibitors with High Potency against Human Immunodeficiency Virus-1 and an Improved human Ether-a-go-go Related Gene (hERG) Profile
  作者：Wieslaw M. Kazmierski、Don L. Anderson、Christopher Aquino、Brian A. Chauder、Maosheng Duan、Robert Ferris、Terrence Kenakin、Cecilia S. Koble、Dan G. Lang、Maggie S Mcintyre、Jennifer Peckham、Christian Watson、Pat Wheelan、Andrew Spaltenstein、Mary B. Wire、Angilique Svolto、Michael Youngman

  DOI：10.1021/jm200279v

  日期：2011.6.9

  We recently described (J. Med. Chem. 2008, 51, 6538-6546) a novel class of CCR5 antagonists with strong anti-HIV potency. Herein, we detail SAR converting leads 1 and 2 to druglike molecules. The pivotal structural motif enabling this transition was the secondary sulfonamide substituent. Further fine-tuning of the substituent pattern in the sulfonamide paved the way to enhancing potency and bioavailability and minimizing hERG inhibition, resulting in discovery of clinical compound 122 (GSK163929).