2-amino-5-n-propyl-thiophene-3-carbonitrile | 879873-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-amino-5-n-propyl-thiophene-3-carbonitrile
• 英文别名: 2-amino-3-cyano-5-propylthiophene；2-amino-5-propylthiophene-3-carbonitrile
• CAS: 879873-65-1
• 化学式: C₈H₁₀N₂S
• 分子量: 166.247
• InChiKey: IRBIHHKVJOVYCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  311.0±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲酸 、 2-amino-5-n-propyl-thiophene-3-carbonitrile 在 ammonium acetate 作用下， 反应 1.0h， 以93%的产率得到2-formylamino-5-n-propyl-thiophene-3-carbonitrile
  参考文献：
  名称：

  [EN] THIOPHENE CONTAINING ANALOGUES OF FLUCONAZOLE AS ANTIFUNGAL AGENTS AND PROCESS FOR THEIR PREPARATION
  [FR] ANALOGUES DE FLUCONAZOLE CONTENANT DU TIOPHÈNE UTILISÉS EN TANT QU'AGENTS ET PROCÉDÉ D'UTILISATION ASSOCIÉ

  摘要：

  公开号：

  WO2010046912A3

文献信息

• [EN] NOVEL THIENO-PYRIDINE AND THIENO-PYRIMIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2-RECEPTORS<br/>[FR] NOUVEAUX DERIVES DE THIENO-PYRIDINE ET DE THIENO-PYRIMIDINE ET LEUR UTILISATION EN TANT QUE MODULATEURS ALLOSTERIQUES POSITIFS DES RECEPTEURS MGLUR2
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2006030031A1

  公开（公告）日：2006-03-23

  The present invention relates to novel compounds, in particular novel thieno-pyridine and thieno-pyrimidine derivatives according to Formula (I), wherein all radicals are defined in the application. The compounds according to the invention are positive allosteric modulators of metabotropic receptors - subt ype 2 ('mGluR2') which are useful for the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction and diseases in which the mGluR2 subtype of metabotropic receptors is involved. In particular, such diseases are central nervous system disorders selected from the group of anxiety, schizophrenia, migraine, depression, and epilepsy. The invention is also directed to pharmaceutical compositions and processes to prepare such compounds and compositions, as well as to the use of such compounds for the prevention and treatment of such diseases in which mGluR2 is involved.

  本发明涉及新颖化合物，特别是根据式（I）定义的新颖噻吩-吡啶和噻吩-嘧啶衍生物，其中应用中定义了所有基团。根据本发明的化合物是代谢型受体的阳性别构调节剂-亚型2（'mGluR2'），对于治疗或预防与谷氨酸功能障碍相关的神经和精神障碍以及涉及代谢型受体的mGluR2亚型的疾病是有用的。特别是，这些疾病是从焦虑、精神分裂症、偏头痛、抑郁症和癫痫等中枢神经系统障碍组中选择的。本发明还涉及制备这种化合物和组合物的药物组合物和方法，以及利用这种化合物预防和治疗涉及mGluR2的这种疾病。
• Malonic Ester Amide Synthesis: An Efficient Methodology for Synthesis of Amides
  作者：Pankaj S. Mahajan、Jyoti P. Mahajan、Santosh B. Mhaske

  DOI：10.1080/00397911.2012.717671

  日期：2013.9.17

  “malonic ester amide synthesis” has been demonstrated, which uses α-substituted/unsubstituted diethyl malonates for the decarboxylative acylation of various aromatic/heteroaromatic primary/secondary amines to form one-carbon homologated amides, thus providing easy access to amides with odd/even chain lengths and an array of substituents on the alkyl/aryl part while avoiding use of acyl chlorides or peptide

  摘要 已经证明了“丙二酸酯酰胺合成”的通用方法，该方法使用 α-取代/未取代的丙二酸二乙酯对各种芳香族/杂芳香族伯胺/仲胺进行脱羧酰化，形成单碳同系酰胺，从而提供容易获得酰胺的方法。具有奇数/偶数链长和烷基/芳基部分上的一系列取代基，同时避免使用酰氯或肽偶联剂。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要
• [EN] ONE POT ACYLATION OF AROMATIC AMINES<br/>[FR] ACYLATION MONOTOPE D'AMINES AROMATIQUES
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2013008256A1

  公开（公告）日：2013-01-17

  The present invention provides a cost effective, environmental friendly and efficient, one pot decarboxylative acylation of aromatic/heteroaromatic primary /secondary amine using diethyl malonate (DEM) to obtain corresponding homologated amides in good yield with a high degree of purity.

  本发明提供了一种经济、环保且高效的方法，使用乙酸二乙酯（DEM）对芳香/杂环原/次要胺进行一锅脱羧酰化反应，以获得相应的同系物酰胺，产率高且纯度高。
• Novel Thieno-Pyridine and Thieno-Pyrimidine Derivatives and Their Use as Positive Allosteric Modulators of Mglur2-Receptors
  申请人：Imogai Julien Hassan

  公开号：US20070275984A1

  公开（公告）日：2007-11-29

  The present invention relates to novel compounds, in particular novel thieno-pyridine and thieno-pyrimidine derivatives according to Formula (I), wherein all radicals are defined in the application. The compounds according to the invention are positive allosteric modulators of metabotropic receptors—subtype 2 (“mGluR2”) which are useful for the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction and diseases in which the mGluR2 subtype of metabotropic receptors is involved. In particular, such diseases are central nervous system disorders selected from the group of anxiety, schizophrenia, migraine, depression, and epilepsy. The invention is also directed to pharmaceutical compositions and processes to prepare such compounds and compositions, as well as to the use of such compounds for the prevention and treatment of such diseases in which mGluR2 is involved.

  本发明涉及一种新颖的化合物，特别是公式（I）中定义的新颖噻吩-吡啶和噻吩-嘧啶衍生物，其中所有基团在申请中定义。本发明的化合物是代谢型受体亚型2（“mGluR2”）的正向变构调节剂，可用于治疗或预防与谷氨酸功能障碍相关的神经和精神障碍以及涉及代谢型受体mGluR2亚型的疾病。特别是，这些疾病是从焦虑、精神分裂症、偏头痛、抑郁症和癫痫等中枢神经系统疾病组中选择的。本发明还涉及制备这种化合物和制剂的制药组合物和制备过程，以及利用这种化合物预防和治疗涉及mGluR2的疾病。
• 2‐Phenylquinazolin‐4(3<i>H</i>)‐one scaffold as newly designed, synthesized VEGFR‐2 allosteric inhibitors with potent cytotoxicity through apoptosis
  作者：Ranza Elrayess、Mohamed S. Elgawish、Mohamed S. Nafie、Nagat Ghareb、Asmaa S. A. Yassen

  DOI：10.1002/ardp.202200654

  日期：2023.6

  of 3.04, 2.93 µM, respectively, according to in situ cytotoxicity testing. Comparing compounds 15 and 18 to sorafenib, the in vitro VEGFR-2 inhibitory activity displayed encouraging selective efficacy with IC50 values of 13, 67, and 30 nM, respectively. Results of VEGFR-2 inhibition at various ATP concentrations proved that there was no statistically significant difference between the IC50 values, which

  2-phenylquinazolin-4(3 H )-one的新衍生物被设计、合成和生物学评估为有效的变构激酶抑制剂，对 MCF-7 和 HepG2 细胞具有原位细胞毒性。拟议化合物中的化合物15和18对 MCF-7 (IC 50 = 1.35 µM) 和 HepG2 细胞 (IC 50  = 3.24 µM) 显示出良好的抗增殖活性，与索拉非尼相当，IC 50值分别为 3.04、2.93 µM，根据原位细胞毒性测试。将化合物15和18与索拉非尼进行比较，体外 VEGFR-2 抑制活性显示出令人鼓舞的选择性功效，IC 为50值分别为 13、67 和 30 nM。VEGFR-2 在不同 ATP 浓度下的抑制结果证明，IC 50值之间没有统计学上的显着差异，这提高了非 ATP 竞争性结合。化合物15导致凋亡性乳腺癌细胞死亡，S 期细胞周期停滞 55.11 倍，通过上调 P53、Bax、半胱天冬酶