4-methylthio-2-oxo-5,6-dihydro-2H-benzo[b]pyrano[2,3-d]oxepine-3-carbonitrile | 1206525-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4-methylthio-2-oxo-5,6-dihydro-2H-benzo[b]pyrano[2,3-d]oxepine-3-carbonitrile
• 英文别名: 4-Methylsulfanyl-2-oxo-5,6-dihydropyrano[3,2-d][1]benzoxepine-3-carbonitrile
• CAS: 1206525-11-2
• 化学式: C₁₅H₁₁NO₃S
• 分子量: 285.323
• InChiKey: ZXWNBHGMUSSGOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  84.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methylthio-2-oxo-5,6-dihydro-2H-benzo[b]pyrano[2,3-d]oxepine-3-carbonitrile 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 3-amino-5,12,13,13a-tetrahydrobenzo[b]oxepino[4,5-e]pyrazolo[3,4-e][1,2]diazepin-4(1H)-one
  参考文献：
  名称：

  Regioselective synthesis of polycyclic aza-oxa and aza-oxa-thia heteroarenes as Colo-205 and HepG2 carcinoma cells growth inhibitors

  摘要：

  An efficient regioselective synthesis of polycyclic diheteroaryl[b,d]pyrans and diheteroaryl[c,e][1,2]diazepines has been reported through ring transformation reactions of 2-oxo-2,5-dihydrothiochromeno [4,3-b]pyrans (3,4), 2-oxo-5,6-dihydro-2H-benzo[b]pyrano[2,3-d]oxepine/thiepine (8, 9) and 6-oxo-3,6-dihydro-2H-naphtho[1,2-b]pyrano[2,3-d]oxepine (15) by hydrazine, at ambient and reflux temperature. Nine compounds viz 5a,b; 10a,c,d; 12b; 13b; 16 and 1-methylthio-5,6-dihydrobenzo[f]quinoline (0.1-100 mu M) were screened for their cytotoxicity in normal (IEC-6), carcinoma (Colo-205) and HepG2 cell lines. None of the compounds showed cytotoxicity in normal IEC-6 cells while 10a,d and 16 resulted in killing of Colo-205 cells with IC50 ranging 20-60 mu M while 10c and 13b caused killing of HepG2 cells with IC50 values ranging 60-80 mu M concentration. Further, 10a,d and 16 caused apoptosis through a cascade of mitochondrial pathway in Colo-205 cells indicating anticancerous potential against intestinal cancer. Interestingly, compounds 10c and 13b exhibited apoptosis through mitochondrial pathway in HepG2 cells suggesting anticancer activity against hepatic cancer. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.013
• 作为产物：
  描述：

  3,4-二氢-2H-苯并[b]噁嗪-5-酮 、 2-氰-3,3-二(甲硫基)丙烯酸甲酯 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以76%的产率得到4-methylthio-2-oxo-5,6-dihydro-2H-benzo[b]pyrano[2,3-d]oxepine-3-carbonitrile
  参考文献：
  名称：

  顺序合成“ U和Z”形多环杂芳烃的方法†

  摘要：

  合成三类新的杂芳烃，方法是通过顺序融合 萘，苯并/萘并[ b ]奥西平 和硫代环与 吡喃并报道了嘧啶环系统产生“ U和Z”形的结构框架。该方法是基于综合吡喃 熔融中间体 1-甲硫基-3-氧代-5,6-二氢-3 H-苯并[ f ]亚甲基-2-腈（3），4-甲硫基-2-氧代-5,6-二氢-2 ħ苯并/萘并[ b ]吡喃并[2,3- d ]氧杂-3-腈（10，20）和4-甲硫基2-氧代-2,5-二氢硫代色素[4,3- b ]吡喃-3-腈（15）的反应2-四氢萘酮，苯并/萘并[ b ]氧杂环丁酮-5-酮和硫代色素-4-酮与2-氰基-3,3-二甲基硫代丙烯酸甲酯分别。中间体的进一步的缩合3，10，20和15与导致四环“U”的形成脒状4-氨基-2-芳基-7,8-二氢-5-氧代-5- ħ -萘并[2,1- b ] pyrimido [4,5- d ] pyrans（8）和'Z'形的4-氨基-2-芳基-5-氧代-氧代12

  DOI：

  10.1039/c2ob25173f

文献信息

• An Expeditious Concise Synthesis of Benzo[b]pyrano[2,3-d]oxepines and Dibenzo[b,d]oxepines
  作者：Vishnu Tandon、Vishnu Ram、Hardesh Maurya、Balendu Kumar、Brijesh Kumar

  DOI：10.1055/s-0029-1218006

  日期：2009.11

  An efficient concise synthesis of 4-methylthio-2-oxo-5,6-dihydro-2 H-benzo[ B]pyrano[2,3- D]oxepine-3-carbonitriles has beendelineated through condensation-cyclization of 3,4-dihydro-2 H-benzo[ B]oxepin-5(2 H)-ones and methyl 2-cyano-3,3-dimethylthioacrylatein DMF using powdered KOH as a base. A base--induced reactionof 3,4-dihydro-2 H-benzo[ B]oxepin-5(2 H)-ones and6-aryl-4-methylthio-2 H-pyran-2

  4-methylthio-2-oxo-5,6-dihydro-2 H-benzo[B]pyrano[2,3-D]oxepine-3-carbonitriles 的高效简明合成已通过 3,4-二氢-2 H-苯并[B]oxepin-5(2 H)-ones 和甲基 2-氰基-3,3-二甲基硫代丙烯酸酯在 DMF 中使用粉末 KOH 作为碱。3,4-dihydro-2 H-benzo[B]oxepin-5(2H)-ones 和 6-aryl-4-methylthio-2 H-pyran-2-one-3-carbonitrilein 的碱诱导反应在 DMF 中加入粉末状 KOH 得到 (E)- 和 (Z)-2-(4-苯基-5,6-二氢-2H-苯并[B]吡喃并[2,3-D]oxepin-2-的异构混合物ylidene) 乙腈。然而，6-aryl-4-(s EC-amino)-2 H-pyran-2-one-3-carbonitriles