5-(thiophene-2-yl)thieno[2,3-d]pyrimidine-4-yl amine | 949526-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5-(thiophene-2-yl)thieno[2,3-d]pyrimidine-4-yl amine
• 英文别名: 5-thiophen-2-yl-thieno[2,3-d]pyrimidin-4-ylamine；5-(Thiophen-2-yl)thieno[2,3-d]pyrimidin-4-amine；5-thiophen-2-ylthieno[2,3-d]pyrimidin-4-amine
• CAS: 949526-33-4
• 化学式: C₁₀H₇N₃S₂
• 分子量: 233.318
• InChiKey: RZWAOCUKRZXFIX-UHFFFAOYSA-N

物化性质

• 沸点：
  469.6±45.0 °C(Predicted)
• 密度：
  1.490±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(thiophene-2-yl)thieno[2,3-d]pyrimidine-4-yl amine 在 亚硝酸特丁酯 、 一水合肼 、 copper dichloride 作用下， 以 四氢呋喃 、 氯仿 、 乙腈 为溶剂， 生成 3-methyl-1-(5-thiophen-2-yl-thieno[2,3-d]pyrimidin-4-ylamino)-pyrrole-2,5-dione
  参考文献：
  名称：

  Discovery of thienopyrimidine-based FLT3 inhibitors from the structural modification of known IKKβ inhibitors

  摘要：

  Inactivation of the NF-kappa B signaling pathway by inhibition of IKK beta is a well-known approach to treat inflammatory diseases such as rheumatoid arthritis and cancer. Thienopyrimidine-based analogues were designed through modification of the known IKKb inhibitor, SPC-839, and then biologically evaluated. The resulting analogues had good inhibitory activity against both nitric oxide and TNF-alpha, which are well-known inflammatory responses generated by activated NF-kappa B. However, no inhibitory activity against IKK beta was observed with these compounds. The thienopyrimidine-based analogues were subsequently screened for a target kinase, and FLT3, which is a potential target for acute myeloid leukemia (AML), was identified. Thienopyrimidine-based FLT3 inhibitors showed good inhibition profiles against FLT3 under 1 mu M. Overall, these compounds represent a promising family of inhibitors for future development of a treatment for AML. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.058
• 作为产物：
  描述：

  2-[1-(2-噻吩)亚乙基]丙二腈 在 哌啶 、 sulfur 作用下， 以 乙醇 为溶剂， 生成 5-(thiophene-2-yl)thieno[2,3-d]pyrimidine-4-yl amine
  参考文献：
  名称：

  Discovery of thienopyrimidine-based FLT3 inhibitors from the structural modification of known IKKβ inhibitors

  摘要：

  Inactivation of the NF-kappa B signaling pathway by inhibition of IKK beta is a well-known approach to treat inflammatory diseases such as rheumatoid arthritis and cancer. Thienopyrimidine-based analogues were designed through modification of the known IKKb inhibitor, SPC-839, and then biologically evaluated. The resulting analogues had good inhibitory activity against both nitric oxide and TNF-alpha, which are well-known inflammatory responses generated by activated NF-kappa B. However, no inhibitory activity against IKK beta was observed with these compounds. The thienopyrimidine-based analogues were subsequently screened for a target kinase, and FLT3, which is a potential target for acute myeloid leukemia (AML), was identified. Thienopyrimidine-based FLT3 inhibitors showed good inhibition profiles against FLT3 under 1 mu M. Overall, these compounds represent a promising family of inhibitors for future development of a treatment for AML. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.058

文献信息

• A One-Step, Atom Economical Synthesis of Thieno[2,3-<i>d</i> ]pyrimidin-4-amine Derivatives by a Four-Component Reaction
  作者：Taoda Shi、ChristopherJ. Zerio、Jared Sivinski、Andrew J. Ambrose、Kohlson T. Moore、Thomas Buckley、Lynn Kaneko、Mae Zhang、Donna D. Zhang、Eli Chapman

  DOI：10.1002/ejoc.201900414

  日期：2019.6.2

  A Na2HPO4-catalyzed four-component reaction between a ketone, malononitrile, S8 and formamide has been realized for the first time. This reaction provides a concise approach to thieno[2,3-d]pyrimidin-4-amines, previously requiring 5 steps. The utility of this reaction was validated by preparing a multi-targeted kinase inhibitor and an inhibitor of the NRF2 pathway with excellent atom- and step-economy

  首次实现了Na2HPO4催化酮、丙二腈、S8和甲酰胺之间的四组分反应。该反应提供了一种制备噻吩并[2,3-d]嘧啶-4-胺的简洁方法，之前需要 5 个步骤。通过制备具有优异原子经济性和步骤经济性的多靶点激酶抑制剂和 NRF2 途径抑制剂，验证了该反应的实用性。
• WO2007/102679
  申请人：——

  公开号：——

  公开（公告）日：——
• Hosni, Hanaa; Ali; Mustafa, Egyptian Journal of Chemistry, 2010, vol. 53, # 3, p. 385 - 401
  作者：Hosni, Hanaa、Ali、Mustafa

  DOI：——

  日期：——
• [EN] NOVEL THIENOPYRIMIDINE DERIVATIVES OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, PROCESS FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME<br/>[FR] NOUVEAUX DÉRIVÉS DE LA THIÉNOPYRIMIDINE OU LEURS SELS PHARMACOCOMPATIBLES, LEUR PROCÉDÉ DE PRÉPARATION, ET PRÉPARATIONS PHARMACEUTIQUES LES COMPRENANT
  申请人：JE IL PHARMACEUTICAL CO LTD

  公开号：WO2007102679A1

  公开（公告）日：2007-09-13

  [EN] The present invention relates to a novel thienopyrimidine derivative having an excellent anti¬ inflammatory and anti-cancer activity, or a pharmaceutically acceptable salt thereof, a process for the preparation thereof and a pharmaceutical composition comprising the same. The compound according to the present invention strongly inhibits IKB kinase-ß (IKK-ß) involved in the activation of a transcriptional factor, NF-?B, which is associated with inducing various immune and inflammatory diseases, whereby a composition comprising the compound is a useful therapeutic agent against inflammatory diseases, in particular, arthritis and cancer.
  [FR] L'invention porte sur un nouveau dérivé de la thiénopyrimidine présentant une excellente activité anti- inflammatoire et anti-cancéreuse ou ses dérivés pharmacocompatibles, sur son procédé de préparation, et sur des préparations pharmaceutiques les comprenant. Ce composé inhibe fortement la kinase IKB-ß (IKK-ß) impliquée dans l'activation d'un facteur de transcription, le NF-?B, associé à l'induction de différentes maladies immunes et inflammatoires; les préparations le comprenant sont donc utiles contre les maladies inflammatoires dont en particulier l'arthrite et le cancer.
• [EN] PHARMACEUTICAL COMPOSITION FOR TREATING AND PREVENTING LEUKEMIA, CONTAINING THIENOPYRIMIDINE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF<br/>[FR] COMPOSITION PHARMACEUTIQUE PERMETTANT DE TRAITER ET DE PRÉVENIR LA LEUCÉMIE, CONTENANT UN DÉRIVÉ DE THIÉNOPYRIMIDINE OU UN SEL PHARMACEUTIQUEMENT ACCEPTABLE DE CELUI-CI<br/>[KO] 티에노피리미딘 유도체 또는 이의 약학적으로 허용가능한 염을 포함하는 백혈병 치료 및 예방용 약학 조성물
  申请人：UNIV YONSEI IACF

  公开号：WO2015160192A1

  公开（公告）日：2015-10-22

  본 기재는 하기 화학식 1로 표시되는 티에노피리미딘 유도체 또는 이의 약학적으로 허용가능한 염을 포함하는, 백혈병 질환의 예방 또는 치료를 위한 약학적 조성물에 관한 것이다.