4-chloro-3-methylsulphanyl-1-phenyl-pyrazolo[3,4-d]pyrimidine | 1415387-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-chloro-3-methylsulphanyl-1-phenyl-pyrazolo[3,4-d]pyrimidine
• 英文别名: 4-Chloro-3-methylsulfanyl-1-phenylpyrazolo[3,4-d]pyrimidine；4-chloro-3-methylsulfanyl-1-phenylpyrazolo[3,4-d]pyrimidine
• CAS: 1415387-16-4
• 化学式: C₁₂H₉ClN₄S
• 分子量: 276.749
• InChiKey: OBUNCZCSBGLBLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  68.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-3-methylsulphanyl-1-phenyl-pyrazolo[3,4-d]pyrimidine 在 一水合肼 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 7.0h， 生成 4-[2-(4-fluorobenzylidene)hydrazinyl]-3-(methylsulphanyl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  新型吡唑并[3,4- d ]嘧啶衍生物的合成作为潜在的抗乳腺癌药物

  摘要：

  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。

  DOI：

  10.1016/j.ejmech.2012.09.031
• 作为产物：
  描述：

  苯肼,盐酸盐 在 sodium acetate 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 反应 14.0h， 生成 4-chloro-3-methylsulphanyl-1-phenyl-pyrazolo[3,4-d]pyrimidine
  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

• Novel Dual Use of Formamide-POCl₃ Mixture for the Efficient, One-Pot Synthesis of Condensed 2<i>H</i>-Pyrimidin-4-amine Libraries Under Microwave Irradiation
  作者：Kishore S. Jain、Muthu K. Kathiravan、Jitender B. Bariwal、Pratip K. Chaskar、Santosh S. Tompe、Nikhilesh Arya

  DOI：10.1080/00397911.2011.607934

  日期：2013.1.1

  The novel dual use of formamide-POCl3 mixture for the incorporation of a C-N fragment to form the pyrimidine nucleus and its subsequent chlorination in an efficient, one-pot synthesis of potentially bioactive condensed 2H-pyrimidin-4-amine libraries under microwave irradiation (MWI) is reported. The one-pot microwave-assisted synthetic protocol is high-yielding, ecofriendly, rapid, and novel as well as eliminates intermittent work-ups. The protocol can be adapted for the library synthesis of series of a condensed pyrimidines.
• Design, synthesis &amp; evaluation of condensed 2H-4-arylaminopyrimidines as novel antifungal agents
  作者：Kishor S. Jain、Vijay M. Khedkar、Nikhilesh Arya、Prasad V. Rane、Pratip K. Chaskar、Evans C. Coutinho

  DOI：10.1016/j.ejmech.2014.02.066

  日期：2014.4

  A small, focussed library of condensed 2H-4-arylaminopyrimidines, with 3-diversity points, based on an initial design by molecular docking study of this scaffold at the active site of the fungal enzyme of cytochrome P-450 family, lanosterol 14 alpha-demethylase (CYP51) was synthesized through a one-pot green chemical synthetic protocol. The screening of the synthesised compounds for antifungal activity against Candida albicans, Aspergillus fumigatus & Aspergillus niger revealed activity in many of the compounds as comparable to that of fluconazole. Based on the antifungal activity and physicochemical property data of these derivatives, a meaningful SAR has been proposed. (c) 2014 Elsevier Masson SAS. All rights reserved.
• 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。
• COX-1/COX-2 inhibition assays and histopathological study of the new designed anti-inflammatory agent with a pyrazolopyrimidine core
  作者：Eman K.A. Abdelall、Phoebe F. Lamie、Amira K.M. Ahmed、EL-Shaymaa EL-Nahass

  DOI：10.1016/j.bioorg.2019.01.031

  日期：2019.5

  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.