benzoylguanidine hydrochloride | 3166-28-7

• 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: benzoylguanidine hydrochloride
• 英文别名: Benzoyl-guanidin; Hydrochlorid；N-carbamimidoylbenzamide;hydrochloride
• CAS: 3166-28-7
• 化学式: C₈H₉N₃O*ClH
• 分子量: 199.64
• InChiKey: TVAWJXOBZYWQNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.5
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯甲酸甲酯 、 盐酸胍 以18%的产率得到benzoylguanidine hydrochloride
  参考文献：
  名称：

  Synthesis and biological evaluation of aroylguanidines related to amiloride as inhibitors of the human platelet Na+/H+ exchanger

  摘要：

  Pyridine and benzene bioisosteres of amiloride were synthesized and evaluated for their inhibitory Potency against the sodium-hydrogen exchanger (NHE) involved in intracellular pH regulation. The inhibition of NHE was determined by using the platelet swelling assay (PSA) in which the swelling of human platelets was induced by their incubation in an acid buffer (pH 6.7). Additionally, the inhibitory potency of the most active compounds was assessed by measuring the inhibition of the EIPA-sensitive Na-22 (+) uptake (UIA) by human platelets after intracellular acidosis. The results indicated that several benzene derivatives and compounds bearing an carbonylguanidine moiety in the meta position of the pyridine nitrogen were much more potent than amiloride (PSA:IC50 = 43.5 muM, UIA:IC50 = 100.1 muM), but less than EIPA, a pyrazine NHE inhibitor (PSA:IC50=0.08 muM, UIA: IC50 - 0.5 muM). In both biological assays (2-amino-5-bromo-pyridine-3-carbonyl)guanidine (32) was the most active molecule (PSA: IC50 = 0.8 muM, UIA : IC50 = 0.8 muM). Our investigations demonstrated that the replacement of the pyrazine ring of amiloride e by a pyridine ora phenyl ring improved the NHE inhibitory potency (phenyl >pyridine >pyrazine). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00022-6

文献信息

• Synthesis and preliminary evaluation of amiloride analogs as inhibitors of the urokinase-type plasminogen activator (uPA)
  作者：Hayden Matthews、Marie Ranson、Joel D.A. Tyndall、Michael J. Kelso

  DOI：10.1016/j.bmcl.2011.09.044

  日期：2011.11

  A known side-activity of the oral potassium-sparing diuretic drug amiloride is inhibition of the enzyme urokinase-type plasminogen activator (uPA, K-i = 7 mu M), a promising anticancer target. Several studies have demonstrated significant antitumor/metastasis properties for amiloride in animal cancer models and it would appear that these arise, at least in part, through inhibition of uPA. Selective optimization of amiloride's structure for more potent inhibition of uPA and loss of diuretic effects would thus appear as an attractive strategy towards novel anticancer agents. The following report is a preliminary structure-activity exploration of amiloride analogs as inhibitors of uPA. A key finding was that the well-studied 5-substituted analogs ethylisopropyl amiloride (EIPA) and hexamethylene amiloride (HMA) are approximately twofold more potent than amiloride as uPA inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of aroylguanidines related to amiloride as inhibitors of the human platelet Na+/H+ exchanger
  作者：D Laeckmann

  DOI：10.1016/s0968-0896(02)00022-6

  日期：2002.6

  Pyridine and benzene bioisosteres of amiloride were synthesized and evaluated for their inhibitory Potency against the sodium-hydrogen exchanger (NHE) involved in intracellular pH regulation. The inhibition of NHE was determined by using the platelet swelling assay (PSA) in which the swelling of human platelets was induced by their incubation in an acid buffer (pH 6.7). Additionally, the inhibitory potency of the most active compounds was assessed by measuring the inhibition of the EIPA-sensitive Na-22 (+) uptake (UIA) by human platelets after intracellular acidosis. The results indicated that several benzene derivatives and compounds bearing an carbonylguanidine moiety in the meta position of the pyridine nitrogen were much more potent than amiloride (PSA:IC50 = 43.5 muM, UIA:IC50 = 100.1 muM), but less than EIPA, a pyrazine NHE inhibitor (PSA:IC50=0.08 muM, UIA: IC50 - 0.5 muM). In both biological assays (2-amino-5-bromo-pyridine-3-carbonyl)guanidine (32) was the most active molecule (PSA: IC50 = 0.8 muM, UIA : IC50 = 0.8 muM). Our investigations demonstrated that the replacement of the pyrazine ring of amiloride e by a pyridine ora phenyl ring improved the NHE inhibitory potency (phenyl >pyridine >pyrazine). (C) 2002 Elsevier Science Ltd. All rights reserved.
• Korndoerfer, Archiv der Pharmazie, 1903, vol. 241, p. 468
  作者：Korndoerfer

  DOI：——

  日期：——