2-Ethyl-3,4,5,6,7,8-hexahydro-4-oxobenzothieno<2,3-d>pyrimidin | 85944-23-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 2-Ethyl-3,4,5,6,7,8-hexahydro-4-oxobenzothieno<2,3-d>pyrimidin
• 英文别名: 2-ethyl-5,6-tetramethylenethieno<2,3-d>pyrimidin-4(3H)-one；2-ethyl-5,6,7,8-tetrahydrothieno[2,3-d]pyrimidin-4(3H)-one；2-ethyl-5,6,7,8-tetrahydro-3H-[1]benzothiolo[2,3-d]pyrimidin-4-one
• CAS: 85944-23-6
• 化学式: C₁₂H₁₄N₂OS
• mdl: MFCD00454939
• 分子量: 234.322
• InChiKey: CHYVJDICXWIFSO-UHFFFAOYSA-N

物化性质

• 沸点：
  442.0±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Ethyl-3,4,5,6,7,8-hexahydro-4-oxobenzothieno<2,3-d>pyrimidin 在 silica gel 、 三乙胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 11.02h， 生成 7-Ethyl-10-thia-3,6,8-triazatetracyclo[7.7.0.02,6.011,16]hexadeca-1(9),2,7,11(16)-tetraene
  参考文献：
  名称：

  Prasad, Mailavaram Raghu; Rao, Akkinepalli Raghu Ram; Rao, Pamulaparthi Shanthan, Synthesis, 2001, # 14, p. 2119 - 2123

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-4,5,6,7-四氢苯并[b]噻吩-3-甲酰胺 在 sodium hydroxide 作用下， 反应 4.0h， 生成 2-Ethyl-3,4,5,6,7,8-hexahydro-4-oxobenzothieno<2,3-d>pyrimidin
  参考文献：
  名称：

  Bohm; Pech, Pharmazie, 1983, vol. 38, # 2, p. 136 - 137

  摘要：

  DOI：

文献信息

• Antihelminthic Activity of Some 2-Substituted Thieno[2,3-d]pyrimidin-4- ones
  作者：Anelia Mavrova、Stefan Dimov、Dimitar Vutchev、Kameliya Anichina、Denitsa Yancheva

  DOI：10.2174/1570180814666171027161555

  日期：2018.6.21

  exhibit higher activity than the reference drugs albendazole and ivermectin at concentrations of 0.37, 0.35 and 0.48 µM resp. 0.92, 0.88 and 1.2 µM after 24-hour incubation of the samples. The highest efficacy at both incubations was revealed by 2-benzyl-5,6,7,8- tetrahydrothieno[2,3-d]pyrimidin-4(3H)-one 2 - 97.94% and 100%, respectively. Compound 15 demonstrated 97.5% antiparasitic activity after 48h

  背景：合理设计生物活性化合物的成功方法之一是生物立体异构策略。因此，噻吩并[2，3-d]嘧啶-4-酮与喹唑啉，胞嘧啶和尿嘧啶的生物立体关系导致产生具有多种生物性质包括抗寄生虫活性的化合物。与哺乳动物相反，所有寄生虫均无法从头合成嘌呤，而是依靠嘌呤挽救途径（PSP）获得嘌呤，这对于它们的生存至关重要。考虑到上述事实，我们设计并合成了一些噻吩并[2,3-d]嘧啶类生物甾醇，以评估其抗旋毛虫病的功效。 方法：通过一锅式环缩合反应，将干燥的氯化氢气体通过2-氨基噻吩-羧酸盐和一系列烷基（分别为芳基）腈作为前体，合成目标化合物。 体外寄生虫学筛选是通过使用旋毛虫的封装感染性幼虫进行的，每1 mL生理溶液100个样本，通过用酸性胃蛋白酶溶液消化预先从肌肉胶囊中释放出来。 结果：合成了十四个2-取代的噻吩并[2,3-d]嘧啶-4-酮并鉴定了其结构。通过抗旋毛虫病筛选获得的数据表明，化合物2、8和15在参考浓度分别为0
• Multistep, Microwave Assisted, Solvent Free Synthesis and Antibacterial Activity of 6-Substituted-2,3,4-trihydropyrimido[1,2-c]9,10,11,12-tetrahydrobenzo[b]thieno[3,2-e]pyrimidines
  作者：Mailavaram Raghu Prasad、Deb Pran Kishore

  DOI：10.1248/cpb.55.776

  日期：——

  by microwave irradiation of equimolar mixture of 4-hydroxythieno[2,3-d]pyrimidines and phosphorus oxychloride. The final compounds were screened for antibacterial activity by Kirby Bauer's method using amicacin as the standard against various gram positive and gram negative bacteria. All the compounds showed antibacterial activity comparable with the standard.

  一种新颖，高效的微波辅助路线，用于合成6-取代的2,3,4-三氢嘧啶[1,2-c] -9,10,11,12-四氢苯并[b]噻吩并[3,2-e已经开发了高产率的]嘧啶。中间体2-取代的4- [3-羟基（丙基-1-氨基）] 5,6,7,8-四氢苯并[b]噻吩并[2,3-d]嘧啶是通过照射2-取代的-在碱性条件下，在微波炉中，将4-氯-5,6,7,8-四氢苯并[b]噻吩并[2,3-d]嘧啶与1-氨基丙醇一起使用。通过微波辐射4-羟基噻吩并[2,3-d]嘧啶和氯氧化磷的等摩尔混合物，合成了4-氯噻吩并[2,3-d]嘧啶。使用氨苄青霉素作为标准品，针对多种革兰氏阳性和革兰氏阴性细菌，通过柯比鲍尔（Kirby Bauer）方法筛选最终化合物的抗菌活性。
• Synthesis of Fused Pyrimidinones by Reaction of Aminoarenecarboxamide with Esters; Preparation of Pyrrolo[2,3-d]-, Thieno[2,3-d]-, Isoxazolo[5,4-d]-, and 1,2,3-Triazolo[4,5-d]-pyrimidinones, and Quinazoles
  作者：Akira Miyashita、Katsuhiro Fujimoto、Tomomi Okada、Takeo Higashino

  DOI：10.3987/com-95-s75

  日期：——

  Several fused pyrimidinones were synthesized by reaction of aminoarenecarboxamide with esters in moderate to good yields. In the presence of sodium ethoxide, treatments of 2-amino-1-phenyl-3-pyrrolecarboxamide(4, 5, and 6), 2-amino-3-thiophene-carboxamide (14), 3-amino-4-isoxazolecarboxamide (10 and 11), 4-amino-1,2,3-triazole-5-carboxamide (16), and o-aminobenzamide (18) with esters (3) such as ethyl formate (3a) and ethyl acetate (3b) led to the corresponding pyrrolo[2,3-d]- (7, 8, and 9), and thieno[2,3-d]pyrimidin-4(3H)-ones (15), isoxazolo[5,4-d]pyrimidin-4(5H)-ones (12 and 13), 1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-ones (17), and 4(3H)-quinazolones (19), respectively.
• Anti-tubercular activities of 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3- d ]pyrimidin-4-amine analogues endowed with high activity toward non-replicative Mycobacterium tuberculosis
  作者：Ganesh Samala、Parthiban Brindha Devi、Shalini Saxena、Saritha Gunda、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmc.2016.09.012

  日期：2016.11

  Thirty three derivatives of 2-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine analogues were synthesized by molecular modification of a reported antimycobacterial molecule (GSK163574A). Compounds were evaluated in vitro against actively replicative and nutrient starved non-replicative Mycobacterium tuberculosis (MTB), enzymatic screening and cytotoxicity against RAW 264.7 cell line. Among the compounds, 2-ethyl-N-phenethy1-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d] pyrimidin-4-amine (5c) was found to be the most active compound against non-replicative MTB with 2.7 log reduction of bacteria at 10 mu g/mL and was more potent than isoniazid (1.2 log reduction) and rifampicin (2.0 log reduction) at same dose level. Compound 5c also showed activity against MTB alanine dehydrogenase enzyme with IC50 of 1.82 +/- 0.42 mu M and showed 25% cytotoxicity against RAW 264.7 cell line at 50 mu g/mL. (C) 2016 Elsevier Ltd. All rights reserved.
• Prasad, M. Raghu; Rao, A. Raghuram; Rao, P. Shanthan, Journal of Chemical Research, Miniprint, 2002, # 1, p. 149 - 153
  作者：Prasad, M. Raghu、Rao, A. Raghuram、Rao, P. Shanthan、Rajan, K. S.

  DOI：——

  日期：——