3-methylsulphanyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one | 91974-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methylsulphanyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one
• 英文别名: 1-Phenyl-3-methylmercapto-pyrazolo<3,4-d>pyrimidon-(4)；3-methylsulfanyl-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one；3-Methylsulfanyl-1-phenylpyrazolo[4,5-e]pyrimidin-4-ol；3-methylsulfanyl-1-phenyl-5H-pyrazolo[3,4-d]pyrimidin-4-one
• CAS: 91974-70-8
• 化学式: C₁₂H₁₀N₄OS
• 分子量: 258.304
• InChiKey: KALVEUDIDRVUDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  84.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methylsulphanyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one 在 一水合肼 、 三乙胺 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 4-ethyl 5-{[3-methylthio-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]methyl}-4H-[1,2,4]triazole-3-thiol
  参考文献：
  名称：

  COX-1/COX-2 inhibition assays and histopathological study of the new designed anti-inflammatory agent with a pyrazolopyrimidine core

  摘要：

  Four pyrazolopyrimidine series were prepared with a substitution at position-4 by Schiff base, triazole, oxadiazole and pyrazole moieties (7a-f, 8a,b, 9a-f, 10a,b and 13a,b), respectively. All the synthesized compounds were evaluated in vitro against COX-2 and in vivo against carrageenan-induced rat paw edema as anti-inflammatory agents. Regarding the anti-inflammatory activity (AI) compounds 7c, 7f, 8a, and 9a showed higher activity with respect to celecoxib. Compounds 9a, 7d, and 7f were closely selective to celecoxib. Also, 7c and 7d were safer than indomethacin and similar to celecoxib as resulted from the histopathological study. In addition, the docking study that showed the binding mode of prominent pyrazolopyrimidine compounds inside the COX-2 receptor. Formation of unexpected pyrazole 13a and 13b was briefly discussed using 2D NMR.

  DOI：

  10.1016/j.bioorg.2019.01.031
• 作为产物：
  描述：

  [双(甲硫基)亚甲基]丙烷二腈 在 sodium acetate 作用下， 反应 10.0h， 生成 3-methylsulphanyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one
  参考文献：
  名称：

  COX-1/COX-2 inhibition assays and histopathological study of the new designed anti-inflammatory agent with a pyrazolopyrimidine core

  摘要：

  Four pyrazolopyrimidine series were prepared with a substitution at position-4 by Schiff base, triazole, oxadiazole and pyrazole moieties (7a-f, 8a,b, 9a-f, 10a,b and 13a,b), respectively. All the synthesized compounds were evaluated in vitro against COX-2 and in vivo against carrageenan-induced rat paw edema as anti-inflammatory agents. Regarding the anti-inflammatory activity (AI) compounds 7c, 7f, 8a, and 9a showed higher activity with respect to celecoxib. Compounds 9a, 7d, and 7f were closely selective to celecoxib. Also, 7c and 7d were safer than indomethacin and similar to celecoxib as resulted from the histopathological study. In addition, the docking study that showed the binding mode of prominent pyrazolopyrimidine compounds inside the COX-2 receptor. Formation of unexpected pyrazole 13a and 13b was briefly discussed using 2D NMR.

  DOI：

  10.1016/j.bioorg.2019.01.031

文献信息

• Synthesis of novel pyrazolo[3,4-d]pyrimidine derivatives as potential anti-breast cancer agents
  作者：Mohammed K. Abd El Hamid、Marko D. Mihovilovic、Hala B. El-Nassan

  DOI：10.1016/j.ejmech.2012.09.031

  日期：2012.11

  A series of new 1-aryl-4-benzylidenehydrazinyl-3-methylsulphanyl-pyrazolo[3,4-d]pyrimidines 6a–p was synthesized. The cytotoxic activity of the newly synthesized compounds against human breast cancer cell line, MCF7 was investigated. Most of the test compounds showed potent antitumor activity comparable to that of doxorubicin. The 1-phenyl series (6a–i) exhibited better antitumor activity than 1-(4-methoxyphenyl)

  合成了一系列新的1-芳基-4-亚苄基肼基-3-甲基磺酰基-吡唑并[3,4- d ]嘧啶6a – p。研究了新合成的化合物对人乳腺癌细胞MCF7的细胞毒活性。大多数测试化合物显示出与阿霉素相当的有效抗肿瘤活性。1-苯基系列（6a – i）表现出比1-（4-甲氧基苯基）系列（6j – p）更好的抗肿瘤活性。4- [2-（4-氟亚苄基）肼基] -3-（甲基磺酰基）-1-苯基-1 H-吡唑并[3,4- d ]嘧啶（6d）是本研究中活性最高的化合物50等于7.5 nM。
• Synthesis of pyrazolo[3,4-<i>d</i>]pyrimidine derivatives using ketene dithioacetals
  作者：Yoshinori Tominaga、Yasumasa Honkawa、Mayumi Hara、Akira Hosomi

  DOI：10.1002/jhet.5570270355

  日期：1990.3

  reaction of ketene dithioacetals 1a,b [1a: bis(methylthiomethylenemalononitrile; 1b: bis(methylthio)methylenecyanoacetamide] with hydrazines (hydrazine hydrate, phenylhydrazine, p-chlorophenylhydrazine, p-nitrophenylhydrazine), with formamide or carbon disulfide proceeded to give the corresponding 4-amino- or 4-hydroxy-3-methylthiopyrazolo[3,4-d]pyrimidines 6a-h in good yields. 3-Aminopyrazolo[3,4-d]pyrimidine

  的5-氨基-3- methylthiopyrazole -4-腈或4-甲酰胺环化3A-J ，这是由乙烯酮二硫反应制备1A，B [1A：双（methylthiomethylenemalononitrile; 1B：二（甲硫基）methylenecyanoacetamide]与肼（水合肼，苯肼，p -chlorophenylhydrazine，p -nitrophenylhydrazine）与甲酰胺或二硫化碳进行，得到相应的4-氨基-或4-羟基-3- methylthiopyrazolo [3,4 d ]嘧啶6A-H在3-氨基吡唑并[3,4- d ]嘧啶衍生物6i-1 通过应用3，5-二氨基吡唑与甲酰胺的环化反应也获得了它们。
• TOMINAGA, YOSHINORI;HONKAWA, YASUMASA;HARA, MAYUMI;HOSOMI, AKIRA, J. HETEROCYCL. CHEM., 27,(1990) N, C. 775-783
  作者：TOMINAGA, YOSHINORI、HONKAWA, YASUMASA、HARA, MAYUMI、HOSOMI, AKIRA

  DOI：——

  日期：——