3-(2H-tetrazol-5-yl)-propionic acid | 100508-42-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2H-tetrazol-5-yl)-propionic acid
• 英文别名: 3-(2H-tetrazol-5-yl)propanoic acid
• CAS: 100508-42-7
• 化学式: C₄H₆N₄O₂
• mdl: MFCD19231929
• 分子量: 142.117
• InChiKey: SSTPUPJGNDJBTO-UHFFFAOYSA-N

物化性质

• 沸点：
  434.3±47.0 °C(Predicted)
• 密度：
  1.555±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3-(2H-tetrazol-5-yl)-propionic 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， 生成 N-[2,4-dimethoxy-5-[(2-methyl-3,4-dihydro-2H-quinolin-1-yl)sulfonyl]phenyl]-3-(2H-tetrazol-5-yl)propanamide
  参考文献：
  名称：

  Inhibitors of the acetyltransferase domain of N-acetylglucosamine-1-phosphate-uridylyltransferase/glucosamine-1-phosphate-acetyltransferase (GlmU). Part 2: Optimization of physical properties leading to antibacterial aryl sulfonamides

  摘要：

  A previously described aryl sulfonamide series, originally found through HTS, targets GlmU, a bifunctional essential enzyme involved in bacterial cell wall synthesis. Using structure-guided design, the potency of enzyme inhibition was increased in multiple isozymes from different bacterial species. Unsuitable physical properties (low Log D and high molecular weight) of those compounds prevented them from entering the cytoplasm of bacteria and inhibiting cell growth. Further modifications described herein led to compounds that possessed antibacterial activity, which was shown to occur through inhibition of GlmU. The left-hand side amide and the right-hand side sulfonamides were modified such that enzyme inhibitory activity was maintained (IC50 <0.1 mu M against GlmU isozymes from Gram-negative organisms), and the lipophilicity was increased giving compounds with Log D -1 to 3. Antibacterial activity in an efflux-pump deficient mutant of Haemophilus influenzae resulted for compounds such as 13. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.003
• 作为产物：
  描述：

  1H-tetrazole-5-propanoic acid methyl ester 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 3-(2H-tetrazol-5-yl)-propionic acid
  参考文献：
  名称：

  [EN] CERTAIN KYNURENINE-3-MONOOXYGENASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF
  [FR] INHIBITEURS DE KYNURÉNINE-3-MONOOXYGÉNASE, COMPOSITIONS PHARMACEUTIQUES ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  本文提供了某些化学实体。包括至少一种化学实体和一种或多种药用可接受载体的制药组合物。描述了治疗对KMO活性抑制敏感的某些疾病和疾病的方法，包括向这些患者施用至少一种化学实体的有效量以减少疾病或疾病的症状的方法。这些疾病包括亨廷顿病等神经退行性疾病。治疗方法包括将至少一种化学实体作为单一活性剂或将至少一种化学实体与一种或多种其他治疗剂结合使用。还提供了筛选能够抑制KMO活性的化合物的方法。

  公开号：

  WO2010011302A1

文献信息

• CERTAIN KYNURENINE-3-MONOOXYGENASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF
  申请人：Wityak John

  公开号：US20110230428A1

  公开（公告）日：2011-09-22

  Certain chemical entities are provided herein. Pharmaceutical compositions comprising at least one chemical entity and one or more pharmaceutically acceptable vehicle. Methods of treating patients suffering from certain diseases and disorders responsive to the inhibition of KMO activity are described, which comprise administering to such patients an amount of at least one chemical entity effective to reduce signs or symptoms of the disease or disorder are disclosed. These diseases include neurodegenerative disorders such as Huntington's disease. Methods of treatment include administering at least one chemical entity as a single active agent or administering at least one chemical entity in combination with one or more other therapeutic agents. Also provided are methods for screening compounds capable of inhibiting KMO activity.

  本文提供了某些化学实体。其中包括至少一种化学实体和一个或多个药学可接受载体的制药组合物。本文还描述了治疗对KMO活性抑制有反应的某些疾病和疾病的方法，包括向这些患者施用至少一种化学实体的数量，以减少疾病或障碍的迹象或症状。这些疾病包括神经退行性疾病，如亨廷顿病。治疗方法包括将至少一种化学实体作为单个活性剂进行施用，或将至少一种化学实体与一个或多个其他治疗剂进行联合施用。此外，还提供了筛选能够抑制KMO活性的化合物的方法。
• Development of a Dihydroquinoline–Pyrazoline GluN2C/2D-Selective Negative Allosteric Modulator of the <i>N</i>-Methyl-<scp>d</scp>-aspartate Receptor
  作者：Michael P. D’Erasmo、Nicholas S. Akins、Peipei Ma、Yao Jing、Sharon A. Swanger、Savita K. Sharma、Perry W. Bartsch、David S. Menaldino、Paul J. Arcoria、Thi-Thien Bui、Alexandre Pons-Bennaceur、Phuong Le、James P. Allen、Elijah Z. Ullman、Kelsey A. Nocilla、Jing Zhang、Riley E. Perszyk、Sukhan Kim、Timothy M. Acker、Azmain Taz、Samantha L. Burton、Kevin Coe、Russell G. Fritzemeier、Nail Burnashev、Hongjie Yuan、Dennis C. Liotta、Stephen F. Traynelis

  DOI：10.1021/acschemneuro.3c00181

  日期：2023.9.6
• [EN] CERTAIN KYNURENINE-3-MONOOXYGENASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS DE KYNURÉNINE-3-MONOOXYGÉNASE, COMPOSITIONS PHARMACEUTIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：CHDI INC

  公开号：WO2010011302A1

  公开（公告）日：2010-01-28

  Certain chemical entities are provided herein. Pharmaceutical compositions comprising at least one chemical entity and one or more pharmaceutically acceptable vehicle. Methods of treating patients suffering from certain diseases and disorders responsive to the inhibition of KMO activity are described, which comprise administering to such patients an amount of at least one chemical entity effective to reduce signs or symptoms of the disease or disorder are disclosed. These diseases include neurodegenerative disorders such as Huntington's disease. Methods of treatment include administering at least one chemical entity as a single active agent or administering at least one chemical entity in combination with one or more other therapeutic agents. Also provided are methods for screening compounds capable of inhibiting KMO activity.

  本文提供了某些化学实体。包括至少一种化学实体和一种或多种药用可接受载体的制药组合物。描述了治疗对KMO活性抑制敏感的某些疾病和疾病的方法，包括向这些患者施用至少一种化学实体的有效量以减少疾病或疾病的症状的方法。这些疾病包括亨廷顿病等神经退行性疾病。治疗方法包括将至少一种化学实体作为单一活性剂或将至少一种化学实体与一种或多种其他治疗剂结合使用。还提供了筛选能够抑制KMO活性的化合物的方法。
• Inhibitors of the acetyltransferase domain of N-acetylglucosamine-1-phosphate-uridylyltransferase/glucosamine-1-phosphate-acetyltransferase (GlmU). Part 2: Optimization of physical properties leading to antibacterial aryl sulfonamides
  作者：Suzanne S. Stokes、Robert Albert、Ed T. Buurman、Beth Andrews、Adam B. Shapiro、Oluyinka M. Green、Andrew R. McKenzie、Ludovic R. Otterbein

  DOI：10.1016/j.bmcl.2012.10.003

  日期：2012.12

  A previously described aryl sulfonamide series, originally found through HTS, targets GlmU, a bifunctional essential enzyme involved in bacterial cell wall synthesis. Using structure-guided design, the potency of enzyme inhibition was increased in multiple isozymes from different bacterial species. Unsuitable physical properties (low Log D and high molecular weight) of those compounds prevented them from entering the cytoplasm of bacteria and inhibiting cell growth. Further modifications described herein led to compounds that possessed antibacterial activity, which was shown to occur through inhibition of GlmU. The left-hand side amide and the right-hand side sulfonamides were modified such that enzyme inhibitory activity was maintained (IC50 <0.1 mu M against GlmU isozymes from Gram-negative organisms), and the lipophilicity was increased giving compounds with Log D -1 to 3. Antibacterial activity in an efflux-pump deficient mutant of Haemophilus influenzae resulted for compounds such as 13. (C) 2012 Elsevier Ltd. All rights reserved.