(4RS)-(±)-3,4-dihydro-6-methyl-4-phenylpyrimidine-2(1H)-thione | 30570-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (4RS)-(±)-3,4-dihydro-6-methyl-4-phenylpyrimidine-2(1H)-thione
• 英文别名: 3,4-Dihydro-4-methyl-6-phenyl-2(1H)-pyrimidinthion；6-methyl-4-phenyl-3,4-dihydro-1H-pyrimidine-2-thione；6-Methyl-4-phenyl-3,4-dihydro-1H-pyrimidine-2-thione
• CAS: 30570-19-5
• 化学式: C₁₁H₁₂N₂S
• 分子量: 204.296
• InChiKey: KHCZLACEZABOFR-UHFFFAOYSA-N

物化性质

• 沸点：
  318.7±52.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4RS)-(±)-3,4-dihydro-6-methyl-4-phenylpyrimidine-2(1H)-thione 在 sulfur 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 氯仿 为溶剂， 生成 4-Methyl-2-methylthio-6-phenylpyrimidin-hydroiodid
  参考文献：
  名称：

  新的2-氨基嘧啶衍生物及其抗锥虫和抗疟原虫活性

  摘要：

  摘要 由无环起始原料，亚苄基丙酮和硫氰酸铵通过5个步骤制备新的2-氨基嘧啶衍生物，包括闭环，芳构化，S-甲基化，氧化成甲基磺酰基化合物以及与合适的胺形成胍。制备的化合物彼此不同之处在于其氨基和其苯环的取代。通过使用微孔板检测法测试了2-氨基嘧啶类药物对睡眠病病原体Trypanosoma brucei rhodesiense以及疟疾病原体恶性疟原虫的体外活性。NF54。用L-6细胞（大鼠骨骼肌成肌细胞）测定其细胞毒性。一些化合物表现出相当好的抗锥虫活性，而另一些则表现出出色的抗血浆活性。讨论了结构修改对这些活动的影响。 图形摘要

  DOI：

  10.1007/s00706-020-02674-7
• 作为产物：
  描述：

  硫脲 、 苄叉丙酮 在 potassium hydroxide 作用下， 生成 (4RS)-(±)-3,4-dihydro-6-methyl-4-phenylpyrimidine-2(1H)-thione
  参考文献：
  名称：

  Analgesic, anticonvulsant and anti-inflammatory activities of some synthesized benzodiazipine, triazolopyrimidine and bis-imide derivatives

  摘要：

  A series of diazipine, pyrimidine, fused triazolopyrimidine and imide derivatives were newly synthesized using 4-phenyl-but-3-en-2-one 1 as a starting material and compounds 2 and 9 are intermediates. Initially the acute toxicity of the compounds was assayed via the determination of their LD50. All the compounds were interestingly less toxic than the reference drug. The pharmacological screening showed that many of these obtained compounds have good analgesic, anticonvulsant and anti-inflammatory activities comparable to Valdecoxib (R), Carbamazepine (R) and Predensilone (R) reference drugs. Regarding the protection against Carrageenan (R) induced edema, five compounds were found more potent than Prednisolone (R). On the other hand, in searching for COX-2 inhibitor, the inhibition of plasma PGE2 for the compounds were determined and four compounds were found more potent than Prednisolone (R). The detailed synthesis, spectroscopic data, pharmacological screening and acute toxicity LD50 for the synthesized compounds were reported. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.07.013

文献信息

• Synthesis of new 4-phenylpyrimidine-2(1 H )-thiones and their potency to inhibit COX-1 and COX-2
  作者：Werner Seebacher、Johanna Faist、Armin Presser、Robert Weis、Robert Saf、Teresa Kaserer、Veronika Temml、Daniela Schuster、Sabine Ortmann、Nadine Otto、Rudolf Bauer

  DOI：10.1016/j.ejmech.2015.07.003

  日期：2015.8

  Several new 4-phenylpyrimidine-2(1H)-thiones have been prepared and investigated for their potencies to inhibit COX-1 and COX-2 enzymes, and COX-2 expression in THP-1 cells. Structure-activity-relationships and physicochemical parameters are discussed. Pharmacophore screening and docking studies were carried out for the most active compound.

  已经制备了几种新的4-苯基嘧啶-2（1 H）-硫酮，并研究了它们抑制THP-1细胞中COX-1和COX-2酶以及COX-2表达的能力。讨论了结构-活性-关系和理化参数。对活性最高的化合物进行了药理学筛选和对接研究。
• Wendelin, Winfried; Schermanz, Karl, Journal of Heterocyclic Chemistry, 1984, vol. 21, # 1, p. 65 - 69
  作者：Wendelin, Winfried、Schermanz, Karl

  DOI：——

  日期：——
• WENDELIN, W.;SCHERMANZ, K., J. HETEROCYCL. CHEM., 1984, 21, N 1, 65-69
  作者：WENDELIN, W.、SCHERMANZ, K.

  DOI：——

  日期：——
• JAENECKE G.; HEIDENHAUSS D.; VOIGT H.; HOFMANN F., WISS. HEFTE PAEDAGOG. HOCHSCH. W. RATKE KOETHEN, 1974, 1(9), NO 1, 73-74
  作者：JAENECKE G.、 HEIDENHAUSS D.、 VOIGT H.、 HOFMANN F.

  DOI：——

  日期：——
• SCHWEIGER K.; ZIGEUNER G., MONATSH. CHEM., 1978, 109, NO 3, 543-550
  作者：SCHWEIGER K.、 ZIGEUNER G.

  DOI：——

  日期：——