N-((1E)-2-(2-thienyl)-1-azavinyl)-2H-benzo[3,4-d]-1,3-dioxolan-5-ylcarboxamide | 1189062-66-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: N-((1E)-2-(2-thienyl)-1-azavinyl)-2H-benzo[3,4-d]-1,3-dioxolan-5-ylcarboxamide
• 英文别名: 3,4-methylenedioxybenzoyl-2-thienylhydrazone；LASSBio 294；LASSBio-294；L-294；(E)-N'-(thiophen-2-ylmethylene)benzo[d][1,3]dioxole-5-carbohydrazide；N-[(E)-thiophen-2-ylmethylideneamino]-1,3-benzodioxole-5-carboxamide
• CAS: 1189062-66-5
• 化学式: C₁₃H₁₀N₂O₃S
• 分子量: 274.3
• InChiKey: YMOJHAPRGAZUPL-VGOFMYFVSA-N

物化性质

• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  88.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-((1E)-2-(2-thienyl)-1-azavinyl)-2H-benzo[3,4-d]-1,3-dioxolan-5-ylcarboxamide 在 溴甲酚绿 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到1,3-benzodioxol-5-carboxylic acid, N'-thiophene-2-ylmethyl-hydrazide
  参考文献：
  名称：

  Synthesis and vasodilatory activity of new N-acylhydrazone derivatives, designed as LASSBio-294 analogues

  摘要：

  Conventional therapy to treat hypertension often involves arterial vasodilation. Decrease of blood pressure by vasodilators is normally associated with adverse effects because of their low vascular selectivity. This is of interest to develop new molecules with potential for clinical use and fewer side effects. Recently, a new bioactive compound of the N-acylhydrazone class, LASSBio294, was shown to produce a cardioinotropic effect and vasodilation. In this report, new derivatives of LASSBio-294 were designed and tested on the contractile response of vascular smooth muscle from Wistar rats. Phenylephrine-induced contracture in the aorta was inhibited by the derivatives LASSBio-785 and LASSBio-788. The concentrations necessary to cause 50% reduction of the maximal vascular response (IC50) were 10.2 +/- 0.5 and 67.9 +/- 6.5 mu M. Vasodilation induced by both derivatives is likely to be mediated by a direct effect on smooth muscle because it was not dependent on the integrity of vascular endothelium. LASSBio-785 was seven times more potent than the reference compound LASSBio-294 (IC50 = 74 mu M) in producing an endothelium-independent vasodilator effect. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.003
• 作为产物：
  描述：

  黄樟素 在 盐酸 、 氢氧化钾 、 碘 、 氧气 、 臭氧 、 一水合肼 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 乙醇 、 正丁醇 为溶剂， 反应 5.5h， 生成 N-((1E)-2-(2-thienyl)-1-azavinyl)-2H-benzo[3,4-d]-1,3-dioxolan-5-ylcarboxamide
  参考文献：
  名称：

  Gonzalez-Serratos, Hugo; Chang, Ruzhang; Pereira, Edna F. R., Journal of Pharmacology and Experimental Therapeutics, 2001, vol. 299, # 2, p. 558 - 566

  摘要：

  DOI：

文献信息

• Studies towards the identification of putative bioactive conformation of potent vasodilator arylidene N-acylhydrazone derivatives
  作者：Arthur E. Kümmerle、Juliana M. Raimundo、Carla M. Leal、Givanildo S. da Silva、Tatiane L. Balliano、Mariano A. Pereira、Carlos A. de Simone、Roberto T. Sudo、Gisele Zapata-Sudo、Carlos A.M. Fraga

  DOI：10.1016/j.ejmech.2009.04.044

  日期：2009.10

  In this report we disclose the synthesis, vasodilatory activity, and identification of bioactive conformation of new N-acylhydrazone and N-methyl-N-acylhydrazone derivatives, structurally designed by bioisosteric replacements of previously described cardioactive compounds LASSBio-294 and its N-methyl derivative LASSBio-785. Some of these novel derivatives presented improved vasorelaxant properties, being new cardiovascular drug candidates. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Selective Muscle Relaxant and Pharmaceutical Compositions
  申请人：Fraga Carlos Alberto Manssour

  公开号：US20080275105A1

  公开（公告）日：2008-11-06

  This invention refers to substances able to cause selective muscle relaxation, pharmaceutical compositions containing such compounds and their use in the treatment of muscle tissue diseases, with such compounds complying with the general formula (I).
• Gonzalez-Serratos, Hugo; Chang, Ruzhang; Pereira, Edna F. R., Journal of Pharmacology and Experimental Therapeutics, 2001, vol. 299, # 2, p. 558 - 566
  作者：Gonzalez-Serratos, Hugo、Chang, Ruzhang、Pereira, Edna F. R.、Castro, Newton G.、Aracava, Yasco、Melo, Paulo A.、Lima, Patricia C.、Fraga, Carlos A. M.、Barreiro, Eliezer J.、Albuquerque, Edson X.

  DOI：——

  日期：——
• Synthesis and vasodilatory activity of new N-acylhydrazone derivatives, designed as LASSBio-294 analogues
  作者：Alexandre G. Silva、Gisele Zapata-Sudo、Arthur E. Kummerle、Carlos A.M. Fraga、Eliezer J. Barreiro、Roberto T. Sudo

  DOI：10.1016/j.bmc.2005.03.003

  日期：2005.5

  Conventional therapy to treat hypertension often involves arterial vasodilation. Decrease of blood pressure by vasodilators is normally associated with adverse effects because of their low vascular selectivity. This is of interest to develop new molecules with potential for clinical use and fewer side effects. Recently, a new bioactive compound of the N-acylhydrazone class, LASSBio294, was shown to produce a cardioinotropic effect and vasodilation. In this report, new derivatives of LASSBio-294 were designed and tested on the contractile response of vascular smooth muscle from Wistar rats. Phenylephrine-induced contracture in the aorta was inhibited by the derivatives LASSBio-785 and LASSBio-788. The concentrations necessary to cause 50% reduction of the maximal vascular response (IC50) were 10.2 +/- 0.5 and 67.9 +/- 6.5 mu M. Vasodilation induced by both derivatives is likely to be mediated by a direct effect on smooth muscle because it was not dependent on the integrity of vascular endothelium. LASSBio-785 was seven times more potent than the reference compound LASSBio-294 (IC50 = 74 mu M) in producing an endothelium-independent vasodilator effect. (c) 2005 Elsevier Ltd. All rights reserved.