1-[6-(噻吩-2-基)吡啶-3-基]甲胺 | 441055-69-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1-[6-(噻吩-2-基)吡啶-3-基]甲胺
• 英文名称: 1-[6-(thiophen-2-yl)pyridin-3-yl]methanamine
• 英文别名: (6-(Thiophen-2-yl)pyridin-3-yl)methanamine；(6-thiophen-2-ylpyridin-3-yl)methanamine
• CAS: 441055-69-2
• 化学式: C₁₀H₁₀N₂S
• 分子量: 190.269
• InChiKey: GFCYCUAXDJPKDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[6-(噻吩-2-基)吡啶-3-基]甲胺 在 N,N-二异丙基乙胺 作用下， 以 丙醇 、 乙二醇 为溶剂， 反应 4.0h， 生成 (R)-2-((3-cyclopentyl-7-(((6-(thiophen-2-yl)pyridin-3-yl)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)amino)butan-1-ol
  参考文献：
  名称：

  新型3,5,7-三取代吡唑并[1,5-a]嘧啶的合成及生物活性评价

  摘要：

  FLT3 蛋白激酶的突变通常与急性髓性白血病中细胞增殖失调有关，抑制该激酶是一种潜在的治疗策略。我们报告了一系列新的 3,5,7-三取代吡唑并 [1,5- a ] 嘧啶，旨在研究它们的生物活性，特别是对 FLT3-ITD 及其下游调节剂以及对 CDK2 和 CDK9 的生物活性。衍生物10b能够强烈抑制所有激酶，其在 FLT3-ITD 表达细胞系 MOLM13 和 MV4-11 中的选择性与 FLT3-ITD 抑制作用一致。进一步的生化分析和分子对接证实 FLT3 是10b的细胞靶标。

  DOI：

  10.1016/j.bmcl.2022.129096

文献信息

• A Novel Series of Highly Potent 2,6,9-Trisubstituted Purine Cyclin-Dependent Kinase Inhibitors
  作者：Tomáš Gucký、Radek Jorda、Marek Zatloukal、Václav Bazgier、Karel Berka、Eva Řezníčková、Tibor Béres、Miroslav Strnad、Vladimír Kryštof

  DOI：10.1021/jm4006884

  日期：2013.8.8

  The inhibition of overactive CDKs during cancer remains an important strategy in cancer drug development. We synthesized and screened a novel series of 2-substituted-6-biarylmethylamino-9-cyclopentylpurine derivatives for improved CDK inhibitory activity and antiproliferative effects. One of the most potent compounds, 6b, exhibited strong cytotoxicity in the human melanoma cell line G361 that correlated with robust CDK1 and CDK2 inhibition and caspase activation. In silico modeling of 6b in the active site of CDK2 revealed a high interaction energy, which we believe is due to the 6-heterobiarylmethylamino substitution of the purine moiety.
• Influence of ligand geometry on cholinesterase enzyme - A comparison of 1-isoindolinone based structural analog with Donepezil
  作者：Sunil P. Upadhyay、Vikas Singh、Ram Sharma、Jianping Zhou、Pritam Thapa、David K. Johnson、Andrew Keightley、Maohui Chen、William Suo、Mukut Sharma

  DOI：10.1016/j.molstruc.2021.131385

  日期：2022.1
• Heterobiaryl purine derivatives as potent antiproliferative agents: Inhibitors of cyclin dependent kinases. Part II
  作者：Michael P. Trova、Keith D. Barnes、Luis Alicea、Travis Benanti、Mark Bielaska、Joseph Bilotta、Brian Bliss、Thuy Nguyen Duong、Simon Haydar、R. Jason Herr、Yu Hui、Matthew Johnson、John M. Lehman、Denise Peace、Matthew Rainka、Patricia Snider、Susan Salamone、Steven Tregay、Xiaozhang Zheng、Thomas D. Friedrich

  DOI：10.1016/j.bmcl.2009.10.011

  日期：2009.12

  C-6 Biarylmethylamino purine derivatives of roscovitine (1) inhibit cyclin dependent kinases and demonstrate potent antiproliferative activity. Replacement of the aryl rings of the C-6 biarylmethylamino group with heterobiaryl rings has provided compounds with significantly improved activity. In particular, derivatives 18g and 9c demonstrated 1000-fold and 1250-fold improvements, respectively, in the growth inhibition of HeLa cells compared to roscovitine (1). (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and biological activity evaluation of novel 3,5,7-trisubstituted pyrazolo[1,5-a]pyrimidines
  作者：Kristýna Vlková、Růžena Padrtová、Tomáš Gucký、Miroslav Peřina、Eva Řezníčková、Vladimír Kryštof

  DOI：10.1016/j.bmcl.2022.129096

  日期：2023.1

  proliferation in acute myeloid leukemia and the inhibition of this kinase is a potential therapeutic strategy. We report a novel series of 3,5,7-trisubstituted pyrazolo[1,5-a]pyrimidines prepared in an effort to study their biological activity particularly toward FLT3-ITD and its downstream regulators as well as toward CDK2 and CDK9. Derivative 10b was capable to strongly inhibit all kinases and its selectivity

  FLT3 蛋白激酶的突变通常与急性髓性白血病中细胞增殖失调有关，抑制该激酶是一种潜在的治疗策略。我们报告了一系列新的 3,5,7-三取代吡唑并 [1,5- a ] 嘧啶，旨在研究它们的生物活性，特别是对 FLT3-ITD 及其下游调节剂以及对 CDK2 和 CDK9 的生物活性。衍生物10b能够强烈抑制所有激酶，其在 FLT3-ITD 表达细胞系 MOLM13 和 MV4-11 中的选择性与 FLT3-ITD 抑制作用一致。进一步的生化分析和分子对接证实 FLT3 是10b的细胞靶标。