4-(4-chlorophenyl)amino-5,6-tetramethylenothieno<2,3-d>pyrimidine | 81136-45-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 4-(4-chlorophenyl)amino-5,6-tetramethylenothieno<2,3-d>pyrimidine
• 英文别名: N-(4-chlorophenyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine；(4-chloro-phenyl)-(5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-yl)-amine；(4-chlorophenyl)-(5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)amine；4-(4-chlorophenyl)amino-5,6-tetramethylenothieno[2,3-d]pyrimidine；N-(4-chlorophenyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-amine
• CAS: 81136-45-0
• 化学式: C₁₆H₁₄ClN₃S
• mdl: MFCD00419586
• 分子量: 315.826
• InChiKey: XODTUAAXWAKVRI-UHFFFAOYSA-N

物化性质

• 熔点：
  136-138 °C
• 沸点：
  516.1±50.0 °C(Predicted)
• 密度：
  1.408±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5,6,7,8-四氢-[1]-苯并噻吩[2,3-d]嘧啶-4(1h)-酮 在 三氯氧磷 作用下， 以 异丙醇 为溶剂， 反应 0.25h， 生成 4-(4-chlorophenyl)amino-5,6-tetramethylenothieno<2,3-d>pyrimidine
  参考文献：
  名称：

  4-取代的噻吩并[2,3-d]嘧啶类作为有效的抗菌剂：合理的设计，微波辅助合成，生物学评估和分子对接研究

  摘要：

  设计，合成4-取代的噻吩并[2,3- d ]嘧啶并评估其抗菌活性。对接研究表明，强效化合物对细菌二氢蝶呤合酶具有抑制活性。因此，还确定了其与DHPS酶的结合亲和力。

  DOI：

  10.1111/cbdd.13028

文献信息

• TRICYCLIC BENZO[4,5]THIENO-[2,3-D]PYRIMIDINE-4-YL-AMIN DERIVATIVES, THEIR SALTS, PROCESS FOR PRODUCING THE COMPOUNDS AND THEIR PHARMACEUTICAL USE
  申请人：Bánhegyi Pèter

  公开号：US20110015214A1

  公开（公告）日：2011-01-20

  The invention relates to novel tricyclic benzo[4,5]thieno-[2,3-d]pyrimidine-4-yl-amin derivatives, as well as their pharmaceutically acceptable salts. The subject of the invention too the process for producing the compounds and their use as a pharmaceutically active agent and as pharmaceutical compositions for prophylaxis and/or treatment of proliferative diseases such as cancer.

  该发明涉及新颖的三环苯并[4,5]噻吩-[2,3-d]嘧啶-4-基-氨基衍生物，以及它们的药学上可接受的盐。该发明还涉及制备这些化合物的方法，以及它们作为药用活性剂和用于预防和/或治疗增殖性疾病如癌症的药物组合物。
• [EN] TRICYCLIC BENZO[4,5]THIENO-[2,3-D]PYRIMIDINE-4-YL-AMIN DERIVATIVES, THEIR SALTS, PROCESS FOR PRODUCING THE COMPOUNDS AND THEIR PHARMACEUTICAL USE<br/>[FR] DÉRIVÉS TRICYCLIQUES DE BENZO[4,5]THIÉNO-[2,3-D]PYRIMIDIN-4-YLAMINE, LEURS SELS, PROCÉDÉ DE FABRICATION DES COMPOSÉS ET LEUR UTILISATION PHARMACEUTIQUE
  申请人：VICHEM CHEMIE KUTATO KFT

  公开号：WO2009104026A1

  公开（公告）日：2009-08-27

  The invention relates to novel tricyclic benzo[4,5]thieno-[2,3-d]pyrimidine-4-yl-amin derivatives, as well as their pharmaceutically acceptable salts. The subject of the invention too the process for producing the compounds and their use as a pharmaceutically active agent and as pharmaceutical compositions for prophylaxis and/or treatment of proliferative diseases such as cancer.

  本发明涉及新型三环苯并[4,5]噻吩-[2,3-d]嘧啶-4-基氨基衍生物，以及其药学上可接受的盐。本发明还涉及生产该化合物的方法，以及将其用作药学活性剂和制备用于预防和/或治疗增殖性疾病如癌症的药物组合物。
• Green catalyst access to thieno [2, 3‐b] pyridines derivatives
  作者：Nawel Mehaoui、Souheyla Boudjema、Zahira Kibou、Noureddine Choukchou‐Braham、Abderrahim Choukchou‐Braham

  DOI：10.1002/jhet.4635

  日期：——

  benefits including a quicker reaction time, an easy set-up, and high yields. Spectroscopic data (IR, +H and 13C NMR spectra) have revealed the structural details of all target compounds. The catalyst was characterized by X-ray diffraction, BET and Fourier-transformed infrared spectroscopy. X-ray diffraction showed that PVW was correctly incorporated on an acid activated clays support. In comparison

  目前的研究重点是使用具有 Keggin 结构并负载在酸活化 (PVW/AAM) 上的钨钒磷酸杂多酸 H 4 PW 11 VO 40 ·8 H 2 O (PVW) 合成新取代的 Thieno [2, 3- b] 吡啶衍生物。建议的协议是一种简单、环保的方法，用于在无溶剂反应条件下合成从 3-cyano-2-aminothiopene 获得的 thieno [2,3-b] 嘧啶衍生物作为构建块。使用合成的 PVW/AAM 催化剂实现了取代的 Thieno [2, 3-b] 吡啶衍生物的优异产率 (60%–97%)。目前的工艺提供的好处包括更快的反应时间、简单的设置和高产率。光谱数据（IR，+ H 和13 C NMR 光谱）揭示了所有目标化合物的结构细节。通过X射线衍射、BET和傅里叶变换红外光谱对催化剂进行了表征。X 射线衍射表明 PVW 正确地结合在酸活化粘土载体上。与母体钨钒磷酸相比，PVW
• Ram; Pandey; Vlietinck, Journal of Heterocyclic Chemistry, 1981, vol. 18, # 7, p. 1277 - 1280
  作者：Ram、Pandey、Vlietinck

  DOI：——

  日期：——
• Design, synthesis and biological evaluation of 4-aniline-thieno[2,3-d]pyrimidine derivatives as MNK1 inhibitors against renal cell carcinoma and nasopharyngeal carcinoma
  作者：Min Zhang、Li Jiang、Jia Tao、Zhaoping Pan、Mingyao He、Dongyuan Su、Gu He、Qinglin Jiang

  DOI：10.1016/j.bmc.2019.04.022

  日期：2019.6

  MAP Kinase Interacting Serine/Threonine Kinase 1 (MNK1) play important roles in the signaling transduction of MAPK pathways. It is significantly overexpressed in renal clear cell carcinoma and head-neck squamous cell carcinoma tissues in both mRNA and protein levels. Based on the crystallographic structure of MNK1 protein and binding modes analysis of known MNK inhibitors, we have designed and synthesized a series of 4-aniline-thieno [2,3-d] pyrimidine derivatives as potential MNK1 inhibitors. These synthetic compounds are tested in biochemical and cell proliferation assays, and six of them display potent inhibitory capacity against MNK1 kinase and cancer cell lines. Compound 12dj with strongest inhibitory capacity is transferred to molecular mechanism studies, and the results indicated that 12dj remarkably suppresses the phosphorylation of EIF4E, a substrate of MNK1. And the expression levels of MNK1, ERK1/2 and pERK1/2 are not affected by compound 12dj incubation in SUNE-1 and 786-O cells. In summary, our works suggested that these novel 4-aniline-thieno[2,3-d]pyrimidine based MNK1 inhibitors might be attractive lead compounds for targeted therapy of renal cell carcinoma and nasopharyngeal carcinoma.