ethyl 2-[(hydrazinocarbonothioyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate | 151094-88-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: ethyl 2-[(hydrazinocarbonothioyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate
• 英文别名: 4-(4,5,6,7-tetrahydro-3-carboethoxy-1-benzothien-2-yl)thiosemicarbazide；Ethyl 2-(aminocarbamothioylamino)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate
• CAS: 151094-88-1
• 化学式: C₁₂H₁₇N₃O₂S₂
• 分子量: 299.418
• InChiKey: VRFMDMMXYOGAPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(hydrazinocarbonothioyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 <(3,4,5,6,7,8-hexahydro-3-amino-4-oxo<1>benzothieno<2,3-d>pyrimidin-2-yl)thio>acetic acid ethyl ester
  参考文献：
  名称：

  Synthesis of 2,3,5,6,7,8-Hexahydro-3-amino-2-thioxo[1]benzothieno[2,3-d]pyrimidin-4(1H)-one and Derivatives of the New Heterocyclic System 7,8,9,10-Tetrahydro-3H,11H-[1]benzothieno[2',3':4,5]pyrimido[2,1-b][1,3,4]thiadiazin-11-one

  摘要：

  A versatile compound, 2,3,5,6,7,8-hexahydro-3-amino-2-thioxo[1]benzothieno [2,3-d]pyrimidin-4(1H)-one (4), was synthesized from ethyl 4,5,6,7-tetrahydro-2-isothiocyanato-1-benzothiophene-3-carboxylate(1). Derivatives of a heterocyclic linear system having the 1,3,4-thiadiazine ring were obtained from the key intermediate (4).

  DOI：

  10.3987/com-92-6304
• 作为产物：
  描述：

  2-异硫氰基-4,5,6,7-四氢-1-苯并噻吩-3-羧酸乙酯 在 一水合肼 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以45%的产率得到ethyl 2-[(hydrazinocarbonothioyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate
  参考文献：
  名称：

  3-氨基-2-thioxo-2,3-二氢噻吩并[2,3- d ]嘧啶-4（1 H）-one，潜在的cox-2选择性抑制剂的桥头甲烷甲烷磺酰胺衍生物的合成方法

  摘要：

  合成了3-氨基-2-硫代-2,3-二氢噻吩并[2,3- d ]嘧啶-4（1 H）-一的甲烷磺酰胺衍生物，一种潜在的选择性COX-2抑制剂，并在此报道了其结构解析。在某些体外实验中，浓度为10μM的某些衍生物显示出显着的抑制百分比。

  DOI：

  10.1002/jhet.5570430443

文献信息

• Synthetic approaches to bridgehead nitrogen methanesulfonamide derivatives of 3-amino-2-thioxo-2,3-dihydrothieno[2,3-<i>d</i>]pyrimidin-4(1<i>H</i>)-ones, potential cox-2 selective inhibitors
  作者：Giuseppe Granata、Salvatore Barbagallo、Antonio Perdicaro、Agostino Marrazzo、Andrea Santagati、Laura Lombardo、Venera Cardile

  DOI：10.1002/jhet.5570430443

  日期：2006.7

  Methane sulfonamide derivatives of 3-amino-2-thioxo-2,3-dihydrothieno[2,3-d]pyimidin-4(1H)-one, potential selective COX-2 inhibitors, were synthesized and their structural elucidation is here reported. Some derivatives, at 10 μM concentration, showed a significant percentage of inhibition in some in vitro experiments.

  合成了3-氨基-2-硫代-2,3-二氢噻吩并[2,3- d ]嘧啶-4（1 H）-一的甲烷磺酰胺衍生物，一种潜在的选择性COX-2抑制剂，并在此报道了其结构解析。在某些体外实验中，浓度为10μM的某些衍生物显示出显着的抑制百分比。
• Discovery of a Novel 5-HT₃ Antagonist/5-HT_1A Agonist 3-Amino-5,6,7,8-tetrahydro-2-{4-[4-(quinolin-2-yl)piperazin-1-yl]butyl}quinazolin-4(3<i>H</i>)-one (TZB-30878) as an Orally Bioavailable Agent for Irritable Bowel Syndrome
  作者：Akira Asagarasu、Teruaki Matsui、Hiroyuki Hayashi、Satoru Tamaoki、Yukinao Yamauchi、Kouichi Minato、Michitaka Sato

  DOI：10.1021/jm1002292

  日期：2010.11.11

  We have prepared a series of quinazolinone derivatives linked with piperazinylquinoline for the treatment of irritable bowel syndrome (IBS). Using pharmacophore analysis, we designed and synthesized compounds which bind to both serotonin receptor subtype 1A (5-HT1A) and subtype 3 (5-HT3). Quinazolinone derivatives with a sulfur atom in the linker showed high affinity in in vitro assays, but low in vivo activity. Focusing on the linker to improve the pharmacokinetic profile, the sulfur atom in the linker was replaced with a methylene group. Further optimization led to the discovery of compound 17m (TZB-30878) (J. Pharmacol. Exp. Ther. 2007, 322, 1315-1323, Patent WO2005082887 (A1), 2005), a novel 5-HT1A agonist/5-HT3 antagonist in the 3-aminoquinazolinone series. In in vivo functional assays, 17m dose dependently inhibited the Bezold-Jarisch reflex and induced 5-HT1A-mediated behaviors, and in an IBS animal model, 17m significantly inhibited stress-induced defecation. Pretreatment by WAY-100635 (5-HT1A antagonist) significantly attenuated but did not abolish the inhibitory effects of 17m. These results suggested that 17m exerted inhibitory effects via both 5-HT1A agonistic and 5-HT3 antagonistic activities and that 17m would be useful as a therapeutic agent for IBS.
• Synthesis of 2,3,5,6,7,8-Hexahydro-3-amino-2-thioxo[1]benzothieno[2,3-d]pyrimidin-4(1H)-one and Derivatives of the New Heterocyclic System 7,8,9,10-Tetrahydro-3H,11H-[1]benzothieno[2',3':4,5]pyrimido[2,1-b][1,3,4]thiadiazin-11-one
  作者：Andrea Santagati、Maria Santagati、Maria Modica

  DOI：10.3987/com-92-6304

  日期：——

  A versatile compound, 2,3,5,6,7,8-hexahydro-3-amino-2-thioxo[1]benzothieno [2,3-d]pyrimidin-4(1H)-one (4), was synthesized from ethyl 4,5,6,7-tetrahydro-2-isothiocyanato-1-benzothiophene-3-carboxylate(1). Derivatives of a heterocyclic linear system having the 1,3,4-thiadiazine ring were obtained from the key intermediate (4).