5-butyl-2-phenyltriazol-3-one | 5133-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-butyl-2-phenyltriazol-3-one
• 英文别名: 5-butyl-2-phenyl-2,4-dihydro-3H-1,2,4-triazol-3-one；1-Phenyl-3-n-butyl-Δ²-1,2,4-triazolin-5-on；3-Butyl-1-phenyl-Δ²-1,2,4-triazolin-5-on；3-n-Butyl-1-phenyl-Δ²-1,2,4-triazolin-5-on；5-n-Butyl-2,4-dihydro-2-phenyl-3H-1,2,4-triazol-3-one；5-butyl-2-phenyl-2,4-dihydro-[1,2,4]triazol-3-one；5-Oxo-3-butyl-1-phenyl-4.5-dihydro-1.2.4-triazol；5-butyl-2-phenyl-4H-1,2,4-triazol-3-one
• CAS: 5133-69-7
• 化学式: C₁₂H₁₅N₃O
• 分子量: 217.271
• InChiKey: UQKOWYYBLGSUHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-butyl-2-phenyltriazol-3-one 在 sodium hydride 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.83h， 生成 5-butyl-2-phenyl-4-<<2-(1H-tetrazol-5-yl)<1,1'-biphenyl>-4'-yl>methyl>-1H-1,2,4-triazol-3-one
  参考文献：
  名称：

  Triazolinones as nonpeptide angiotensin II antagonists. 1. Synthesis and evaluation of potent 2,4,5-trisubstituted triazolinones

  摘要：

  A series of 2,4-dihydro-2,4,5-trisubstituted-3H-1,2,4-triazol-3-ones was prepared via several synthetic routes and evaluated as AII receptor antagonists in vitro and in vivo. The preferred compounds contained a [2'-(5-tetrazolyl)biphenyl-4-yl]methyl side chain at N4 and an n-butyl group at C5. A number of these bearing an alkyl or aralkyl substituent at N2 showed in vitro potency in the nanomolar range (rabbit aorta membrane receptor), and several of these, e.g., the 2,2-dimethyl-1-propyl analogue (54, IC50 = 2.1 nM), effectively blocked the AII pressor response in conscious rats with significant duration (2.5 h at 1 mg/kg orally for 54). Among analogues possessing aryl substituents at N2, ortho substitution on the phenyl moiety resulted in several derivatives with in vitro potency in the low nanomolar range. One of these, featuring a 2-(trifluoromethyl)phenyl substituent at N2 (25, IC50 = 1.2 nM), was effective at 1 mg/kg orally in the rat model, with a duration of >6 h. Implications for hydrophobic and hydrogen-bonding interactions with the AT1 receptor are discussed.

  DOI：

  10.1021/jm00069a015
• 作为产物：
  描述：

  ethyl N-carbethoxy-valerimidate 在 三乙胺 、 苯肼 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以252 mg (58%)的产率得到5-butyl-2-phenyltriazol-3-one
  参考文献：
  名称：

  Substituted triazolinones, triazolinethiones, and triazolinimines as

  摘要：

  已披露了新的取代三唑酮，三唑硫酮和三唑亚胺化合物，这些化合物可用作血管紧张素II拮抗剂。这些化合物具有一般式：##STR1## 其中G为R.sup.1或##STR2##

  公开号：

  US05411980A1

文献信息

• Substituted 1,2,4-triazoles bearing acidic functional groups as
  申请人：Merck & Co., Inc.

  公开号：US05281614A1

  公开（公告）日：1994-01-25

  Novel substituted triazolinone, triazolinethione, and triazolinimine compounds of the formula I are useful as angiotensin II antagonists. ##STR1##

  这些公式I中的新型替代三唑酮，三唑硫酮和三唑亚胺化合物可用作抗血管紧张素II拮抗剂。
• Substituted triazolinones, triazolinethiones, and triazolinimines as angiotensin II antagonists
  申请人：MERCK & CO. INC.

  公开号：EP0412594A2

  公开（公告）日：1991-02-13

  There are disclosed new substituted triazolinone, triazolinethione, and triazolinimine compounds which are useful as angiotensin II antagonists. These compounds have the general formula:

  公开了可用作血管紧张素 II 拮抗剂的新的取代三唑啉酮、三唑啉硫酮和三唑啉亚胺化合物。这些化合物的通式如下
• Synthesis and structure-activity relationships of nonpeptide, potent triazolone-based angiotensin II receptor antagonists
  作者：Horng Chih Huang、David B. Reitz、Timothy S. Chamberlain、Gillian M. Olins、Valerie M. Corpus、Ellen G. McMahon、Maria A. Palomo、John P. Koepke、Glenn J. Smits

  DOI：10.1021/jm00067a015

  日期：1993.7

  2,5-Dibutyl-2,4-dihydro-4-[[2-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4'-yl]methyl] -3H-1,2,4-triazol-3-one, SC-51316, was synthesized as a potent and orally active angiotensin II (AII) receptor antagonist with a long duration of action. To explore the lipophilic pocket in the AII receptor interacting with the substituent at the 2-position of triazolone-based antagonists, a series of compounds were prepared and evaluated for receptor binding affinity and antagonism of AII-contracted rabbit aortic rings. It has been found that the pocket is very spacious and can accommodate different sizes of lipophilic groups and various functionalities. Acidic groups generally result in a slight decrease in binding affinity. Branched chains are unfavorable. The freedom of rotation around C2-C3 in the flexible side chain is crucial for good binding. The 2-phenylethyl-substituted triazolone analogue exhibits the highest in vitro potency among all compounds that have been synthesized.
• ACIDIC ARALKYL TRIAZOLE DERIVATIVES ACTIVE AS ANGIOTENSIN II ANTAGONISTS
  申请人：MERCK & CO. INC.

  公开号：EP0586513A1

  公开（公告）日：1994-03-16
• US5281614A
  申请人：——

  公开号：US5281614A

  公开（公告）日：1994-01-25