ethyl 4,5-dimethyl-2-(1H-tetrazol-1-yl)thiophene-3-carboxylate | 332163-80-1

• 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 4,5-dimethyl-2-(1H-tetrazol-1-yl)thiophene-3-carboxylate
• 英文别名: 4,5-Dimethyl-2-tetrazol-1-yl-thiophene-3-carboxylic acid ethyl ester；ethyl 4,5-dimethyl-2-(tetrazol-1-yl)thiophene-3-carboxylate
• CAS: 332163-80-1
• 化学式: C₁₀H₁₂N₄O₂S
• 分子量: 252.297
• InChiKey: HJGNQCLDKFXSBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  98.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 4,5-dimethyl-2-(1H-tetrazol-1-yl)thiophene-3-carboxylate 在 一水合肼 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 11-Anilino-4,5-dimethyl-6-thia-1,8,10,12-tetrazatricyclo[7.3.0.03,7]dodeca-3(7),4,8,10-tetraen-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of thieno [2′,3′:4,5]pyrimido[1,2-b][1,2,4]triazines and thieno[2,3-d][1,2,4]triazolo[1,5-a]pyrimidines as anti-inflammatory and analgesic agents

  摘要：

  A new series of thieno[2',3':4,5]pyrimido[1,2-b][1,2,4]triazines and thieno[2,3-d][1,2,4]triazolo[1,5-a] pyrimidines was synthesized. The newly synthesized compounds were evaluated for their anti-inflammatory and analgesic activity using diclofenac Na as a reference standard. Additionally, the ulcerogenic effects and acute toxicity (ALD(50)) values of the active compounds were also determined. In general, the thieno[2,3-d][1,2,4]triazolo[1,5-a]pyrimidine derivatives exhibited better biological activities than the thieno[2',3':4,5]pyrimido[1,2-b][1,2,4]triazines. Collectively, the thienotriazolopyrimidine derivatives 9, 13 and 14a were proved to display distinctive anti-inflammatory activity at the acute and subacute models as well as good analgesic profile with a delayed onset of action. Moreover, they revealed good gastrointestinal safety profile and are well tolerated by experimental animals with high safety margin (ALD(50) > 0.3 g/kg). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.003
• 作为产物：
  描述：

  原甲酸三乙酯 、 2-氨基-4,5-二甲基噻吩-3-羧酸乙酯 在 盐酸 、 sodium azide 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以65%的产率得到ethyl 4,5-dimethyl-2-(1H-tetrazol-1-yl)thiophene-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of thieno [2′,3′:4,5]pyrimido[1,2-b][1,2,4]triazines and thieno[2,3-d][1,2,4]triazolo[1,5-a]pyrimidines as anti-inflammatory and analgesic agents

  摘要：

  A new series of thieno[2',3':4,5]pyrimido[1,2-b][1,2,4]triazines and thieno[2,3-d][1,2,4]triazolo[1,5-a] pyrimidines was synthesized. The newly synthesized compounds were evaluated for their anti-inflammatory and analgesic activity using diclofenac Na as a reference standard. Additionally, the ulcerogenic effects and acute toxicity (ALD(50)) values of the active compounds were also determined. In general, the thieno[2,3-d][1,2,4]triazolo[1,5-a]pyrimidine derivatives exhibited better biological activities than the thieno[2',3':4,5]pyrimido[1,2-b][1,2,4]triazines. Collectively, the thienotriazolopyrimidine derivatives 9, 13 and 14a were proved to display distinctive anti-inflammatory activity at the acute and subacute models as well as good analgesic profile with a delayed onset of action. Moreover, they revealed good gastrointestinal safety profile and are well tolerated by experimental animals with high safety margin (ALD(50) > 0.3 g/kg). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.003

文献信息

• New Convenient Strategy for Annulation of Pyrimidines to Thiophenes or Furans via the One-pot Multistep Cascade Reaction of 1<i>H</i>-Tetrazoles with Aliphatic Amines
  作者：Nazariy T. Pokhodylo、Olga Ya. Shyyka、Vasyl S. Matiychuk、Mykola D. Obushak

  DOI：10.1021/co5001376

  日期：2015.7.13

  high-yield synthetic method for 2-R(3),R(4)-amino-5-R(1)-6-R(2)-thieno[2,3-d]pyrimidin-4(3H)-ones, 2-R(3),R(4)-amino-5-R(1)-6-R(2)-thieno[3,2-d]pyrimidin-4(3H)-ones, and benzofuro[3,2-d]pyrimidin-4(3H)-ones preparation has been developed. The reaction proceeded without using solvents and included several steps. A variety of thieno[2,3-d]pyrimidine and thieno[3,2-d]pyrimidine derivatives with substituents

  一种通用，便捷，高效且高产率的2-R（3），R（4）-氨基-5-R（1）-6-R（2）-噻吩并[2,3-d]嘧啶合成方法-4（3H）-ones，2-R（3），R（4）-amino-5-R（1）-6-R（2）-thieno [3,2-d]嘧啶-4（3H） -ones和苯并呋喃[3,2-d]嘧啶-4（3H）-ones制剂已经开发出来。反应在不使用溶剂的情况下进行，包括几个步骤。从取代的烷基2-（1H-四唑-1-基）噻吩-3高收率获得了各种具有不同性质取代基的噻吩并[2,3-d]嘧啶和噻吩并[3,2-d]嘧啶衍生物用脂肪族胺处理后，分别生成-羧酸盐，3-（1H-四唑-1-基）噻吩-2-羧酸酯和3-（1H-四唑-1-基）苯并呋喃-2-羧酸酯。
• Cage-Like Amines in the Green Protocol of Transannular Thieno[2,3-d]Pyrimidinone Formation as Promising Anticancer Agents
  作者：Olga Ya. Shyyka、Nazariy T. Pokhodylo、Vitalii A. Palchykov、Nataliya S. Finiuk、Rostyslav S. Stoika、Mykola D. Obushak

  DOI：10.1007/s10593-020-02732-2

  日期：2020.6

  bioisostere of the 2-arylamino moiety. Preliminary screening of the biological activity was performed and 2-[1-(bicyclo[2.2.1]heptan-2-yl)ethyl]amino}-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one demonstrated high toxicity toward human leukemia HL-60, cervix carcinoma KB3-1, and colon carcinoma HCT116 cells that correlates well with the results obtained previously for the activity of

  在一个通用的，方便的一锅绿色合成实验中研究了具有降冰片烷和金刚烷骨架的笼状胺，用于通过1 H-四唑环的裂解来嘧啶核的环化。在优化条件下进行转环反应时，无需过量的试剂和溶剂。结果，以高收率获得了11个具有大取代基的新的噻吩并[2,3- d ]嘧啶酮，而无需进一步纯化，并且该方法具有优异的选择性。引入的类似age的框架被认为是2-芳基氨基部分的生物等排体。进行生物活性的初步筛选和2 - [1-（二环[2.2.1]庚-2-基）乙基]氨基} -5,6,7,8-四氢[1]苯并噻吩并[2,3 --d ]嘧啶-4（3 H）-1对人白血病HL-60，子宫颈癌KB3-1和结肠癌HCT116细胞显示出高毒性，这与先前获得的具有苄基氨基取代基的化合物的活性相关。
• Synthesis and biological evaluation of thieno [2′,3′:4,5]pyrimido[1,2-b][1,2,4]triazines and thieno[2,3-d][1,2,4]triazolo[1,5-a]pyrimidines as anti-inflammatory and analgesic agents
  作者：Hayam M. Ashour、Omaima G. Shaaban、Ola H. Rizk、Ibrahim M. El-Ashmawy

  DOI：10.1016/j.ejmech.2012.12.003

  日期：2013.4

  A new series of thieno[2',3':4,5]pyrimido[1,2-b][1,2,4]triazines and thieno[2,3-d][1,2,4]triazolo[1,5-a] pyrimidines was synthesized. The newly synthesized compounds were evaluated for their anti-inflammatory and analgesic activity using diclofenac Na as a reference standard. Additionally, the ulcerogenic effects and acute toxicity (ALD(50)) values of the active compounds were also determined. In general, the thieno[2,3-d][1,2,4]triazolo[1,5-a]pyrimidine derivatives exhibited better biological activities than the thieno[2',3':4,5]pyrimido[1,2-b][1,2,4]triazines. Collectively, the thienotriazolopyrimidine derivatives 9, 13 and 14a were proved to display distinctive anti-inflammatory activity at the acute and subacute models as well as good analgesic profile with a delayed onset of action. Moreover, they revealed good gastrointestinal safety profile and are well tolerated by experimental animals with high safety margin (ALD(50) > 0.3 g/kg). (C) 2012 Elsevier Masson SAS. All rights reserved.