{3-amino-4-[4-(dimethylamino)phenyl]-6-phenylthieno[2,3-b]pyridin-2-yl}(4-chlorophenyl)methanone | 1127227-36-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: {3-amino-4-[4-(dimethylamino)phenyl]-6-phenylthieno[2,3-b]pyridin-2-yl}(4-chlorophenyl)methanone
• 英文别名: [3-Amino-4-[4-(dimethylamino)phenyl]-6-phenylthieno[2,3-b]pyridin-2-yl]-(4-chlorophenyl)methanone
• CAS: 1127227-36-4
• 化学式: C₂₈H₂₂ClN₃OS
• 分子量: 484.021
• InChiKey: CZPZRWDMPLLHPF-UHFFFAOYSA-N

物化性质

• 熔点：
  212-214 °C(Solvent: Ethanol)
• 沸点：
  736.1±60.0 °C(predicted)
• 密度：
  1.318±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  87.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-[4-(dimethylamino)phenyl]-6-phenyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile 、 2'-溴-4-氯苯乙酮 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 生成 {3-amino-4-[4-(dimethylamino)phenyl]-6-phenylthieno[2,3-b]pyridin-2-yl}(4-chlorophenyl)methanone
  参考文献：
  名称：

  Synthesis, Characterization, and Reactions of Pyridine-3-Carbonitrile Derivatives

  摘要：

  2-Thioxopyridine-3-carbonitrile derivatives 6a-c reacted with several halogen containing reagents 7a-d to afford the corresponding thieno[2,3-b]pyridine derivatives 9a-l, respectively. Thieno[2,3-b]pyridines 9c, g,k used for the preparation of their corresponding carbohydrazide derivatives 10a-c which in turn, used as good synthons for the synthesis of N-phenylmethylenethieno[2,3-b]pyridine-2-carbohydrazides 13a-c, pyrido[3',2':4,5]thieno[3,2-d]pyrimidinones 15a-c, 16a-c and 17 and 1,3,4-oxadiazole-2-thiols 20a-c and 21a-c via their reactions with benzaldehyde or benzylidenemalononitrile, triethylorthoformate and carbon disulfide followed by hydrazine hydrate respectively. Considering the data of IR, H-1 NMR, mass spectra, and elemental analyses elucidated the chemical structures of the newly synthesized heterocyclic compounds.

  DOI：

  10.1080/10426500701693552

文献信息

• THIENO [2,3-b] PYRIDINES AS MULTIDRUG RESISTANCE MODULATORS
  申请人：LATVIAN INSTITUTE OF ORGANIC SYNTHESIS

  公开号：US20160137664A1

  公开（公告）日：2016-05-19

  The thieno[2,3-b]pyridines of general formula (I), wherein R 1 is Me, C 6 H 5 , 3,4,5-(OMe) 3 C 6 H 2 , NH 2 ; R 2 is H, CN, COMe, COOC 1-4 alkyl, COOC 2 H 4 OMe, COOC 2 H 4 OPr(n); R 3 is C 6 H 4 R 6 , 3,4-OCH 2 O—C 6 H 3 ; 2-furanyl; R 6 is 4-Cl, 4-NO 2 , 4-N(C 1-4 alkyl) 2 , 3-(C 1-4 alkyloxy), 4-(C 1-4 alkyloxy), 3,4-(C 1-4 alkyloxy) 2 , 3,4,5-(C 1-4 alkyloxy) 3 ; R 4 is NH 2 , NHCOMe; R 5 is CN, COMe, COC 6 H 4 R 7 ; CO-(2-naphthyl); R 7 is H, 4-F, 4-Cl, 3-OMe, 4-OMe, 2,4-(OMe) 2 , 3,4,5-(OMe) 3 as multidrug resistance modulators to increase the effectiveness of chemotherapy in cancer treatment.

  通式为（I）的噻吩[2,3-b]吡啶，其中R1为Me，C6H5，3,4,5-(OMe)3C6H2，NH2; R2为H，CN，COMe，COOC1-4烷基，COOC2H4OMe，COOC2H4OPr(n); R3为C6H4R6，3,4-OCH2O—C6H3; 2-呋喃基; R6为4-Cl，4-NO2，4-N(C1-4烷基)2，3-(C1-4烷氧基)，4-(C1-4烷氧基)，3,4-(C1-4烷氧基)2，3,4,5-(C1-4烷氧基)3; R4为NH2，NHCOMe; R5为CN，COMe，COC6H4R7; CO-(2-萘基); R7为H，4-F，4-Cl，3-OMe，4-OMe，2,4-(OMe)2，3,4,5-(OMe)3，作为多药耐药调节剂，以增加癌症治疗中化疗的有效性。