9-chloro-4-morpholino-2-oxo-2,5-dihydrothiochromeno[4,3-b]pyran-3-carbonitrile | 1353561-55-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻喃类
• 英文名称: 9-chloro-4-morpholino-2-oxo-2,5-dihydrothiochromeno[4,3-b]pyran-3-carbonitrile
• 英文别名: 9-chloro-4-morpholin-4-yl-2-oxo-5H-thiochromeno[4,3-b]pyran-3-carbonitrile
• CAS: 1353561-55-3
• 化学式: C₁₇H₁₃ClN₂O₃S
• 分子量: 360.821
• InChiKey: TXQGQGJTQWUXLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  87.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-chloro-4-morpholino-2-oxo-2,5-dihydrothiochromeno[4,3-b]pyran-3-carbonitrile 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以62%的产率得到3-amino-7-chloro-4,11-dihydro-4-oxo-1H-pyrazolo[4,3-c]thiochromeno[3,4-e]pyran
  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：

  6-氯硫代苯并二氢吡喃-4-酮 在 potassium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 9-chloro-4-morpholino-2-oxo-2,5-dihydrothiochromeno[4,3-b]pyran-3-carbonitrile
  参考文献：
  名称：

  Partially reduced thiochromene based oxathiahelicenes: crystallographic, computational and Hirschfeld surface analyses

  摘要：

  已描述了一种高效简洁的合成路线，通过碱诱导环转化4-sec-氨基-2-氧基-2,5-二氢噻唑烯[4,3-b]吡喃-3-氰基，与噻唑烯-4-酮、1-茚酮和2-茚酮单独反应，构建了外层螺旋上带有杂原子的噻烯基氧螺旋。P和4a的X射线研究显示，通过弱的C–H⋯O和C–H⋯N分子间相互作用形成超分子结构。在6a中观察到通过C–H⋯N和π⋯π的超分子链，而在7中则通过C–H⋯π和π⋯π的弱分子间相互作用。对Hirschfeld表面和指纹图的详细分析提供了一幅新合成化合物中非共价相互作用模式的比较图。利用DFT和AIM理论计算估算了与这些弱相互作用相关的稳定化能。

  DOI：

  10.1039/c3ce41078a

文献信息

• Synthesis of Highly Functionalized Spirobutenolides via a Nitroalkane-Mediated Ring Contraction of 2-Oxobenzo[<i>h</i>]chromenes through Denitration
  作者：Amr Elagamy、Ranjay Shaw、Rahul Panwar、Shally、Vishnu Ji Ram、Ramendra Pratap

  DOI：10.1021/acs.joc.8b02257

  日期：2019.2.1

  spirobutenolides was carried out by a nitroalkane carbanion-induced ring opening and relactonization via a denitration reaction of 2-oxo-5,6-dihydro-2H-benzo[h]chromene-3-carbonitriles and 2-oxo-2,5-dihydrothiochromeno[4,3-b]pyran-3-carbonitriles. However, when nitroethane was used as a nucleophile source in lieu of nitromethane, a mixture of (E)- and (Z)-isomers of the corresponding spirobutenolides

  通过2-烷氧基-5,6-二氢-2 H-苯并[ h ]亚甲基-3-腈和2-腈的反硝化反应，通过硝基烷碳负离子诱导的开环和再乳化，轻松合成高度官能化的螺丁烯内酯氧代2，5-二氢硫代色素[4，3- b ]吡喃-3-腈。然而，当使用硝基乙烷代替硝基甲烷作为亲核试剂源时，以不同的比例获得了相应的螺丁烯内酯的（E）-和（Z）-异构体的混合物。通过单晶X射线衍射确认产物的结构和几何形状。隔离的（E）-和（Z室温下用乙醇钠在DMF中处理的1）-丁烯内酯通过烯丙基开环随后脱羧提供高度取代的三烯。
• Non-catalytic approach to the synthesis of partially reduced ‘S’ shaped dioxathia- and oxadithiahelicenes through base induced inter- and intramolecular C–C bond formation
  作者：Hardesh K. Maurya、Vishnu K. Tandon、Brijesh Kumar、Abhinav Kumar、Volker Huch、Vishnu Ji Ram

  DOI：10.1039/c1ob06091k

  日期：——

  An efficient and convenient route for the construction of helical ‘S’ shaped dioxathia- and oxadithiahelicenes with oxygen and sulfur atoms located in the middle of the outer helix has been developed through base induced inter- and intramolecular C–C bond formation from the reaction of 4-sec-amino-2-oxo-2,5-dihydrothiochromeno[4,3-b]pyran-3-carbonitriles with 3,4-dihydro-2H-benzo[b]oxepin-5(2H)-ones

  通过碱诱导的分子间和分子内碳-碳键的形成，已经开发出了一种有效且便捷的途径，用于在外部螺旋的中部构筑具有氧原子和硫原子的螺旋“ S”形二氧杂硫杂环丁烷和恶二硫杂螺旋。 4-仲丁基-氨基-2-氧代-2,5- dihydrothiochromeno [4,3- b ]吡喃-3-甲腈与3,4-二氢-2 H ^ -苯并[ b ]氧杂-5-（2- ħ） -酮，3,4-二氢苯并[ b ]噻吩-5（2 H）-one和thiochroman-4-ones分别。还进行了量子化学计算，以探索新合成化合物的几何形状和电子结构，以设想两种阻转异构体相互转化的途径。螺旋度参数和构型稳定性的确定表明，能垒强烈地取决于存在的杂原子的性质。
• Sequential approach to the synthesis of ‘U and Z’ shaped polycyclic heteroarenes
  作者：Hardesh K. Maurya、Sanjay K. Gautam、Ramendra Pratap、Vishnu K. Tandon、Abhinav Kumar、Vikas Bajpai、Brijesh Kumar、Vishnu Ji Ram

  DOI：10.1039/c2ob25173f

  日期：——

  sequential fusion of naphthalene, benzo/naphtho[b]oxepine and thiochromene rings with pyran and pyrimidine ring systems to give ‘U and Z’ shaped structural frameworks is reported. The methodology is based on the synthesis of pyran fused intermediates, 1-methylthio-3-oxo-5,6-dihydro-3H-benzo[f]chromene-2-carbonitrile (3), 4-methylthio-2-oxo-5,6-dihydro-2H-benzo/naphtho[b]pyrano[2,3-d]oxepine-3-carbonitriles (10

  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
• Regioselective synthesis of polycyclic aza-oxa and aza-oxa-thia heteroarenes as Colo-205 and HepG2 carcinoma cells growth inhibitors
  作者：Hardesh K. Maurya、Sanjay K. Gautam、Ramendra Pratap、Vishnu K. Tandon、Abhinav Kumar、Brijesh Kumar、Shruti Saxena、Deepti Tripathi、Meenakshi Rajwanshi、Mukul Das、Vishnu Ji Ram

  DOI：10.1016/j.ejmech.2014.05.013

  日期：2014.6

  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.
• Partially reduced thiochromene based oxathiahelicenes: crystallographic, computational and Hirschfeld surface analyses
  作者：Abhinav Kumar、Volker Hüch、Vishnu Ji Ram

  DOI：10.1039/c3ce41078a

  日期：——

  An efficient and concise route for the construction of thiochromene based oxahelicenes in which heteroatoms are located on the outer helix through base-induced ring transformation of 4-sec.amino-2-oxo-2,5-dihydrothiochromeno[4,3-b]pyran-3-carbonitriles by thiochroman-4-one, 1-indanone and 2-indanone separately has been described. The X-ray studies for P and 4a show the formation of supramolecular structures through weak C–H⋯O and C–H⋯N intermolecular interactions. Supramolecular chains in 6a through C–H⋯N and π⋯π and in 7via C–H⋯π and π⋯π weak and intermolecular interactions have been observed. The detail analyses of Hirschfeld surface and fingerprint plots gave a comparative picture of the modes of non-covalent interactions in the newly synthesized compounds. The stabilization energies associated with these weak interactions have been estimated using DFT and AIM theory calculations.

  已描述了一种高效简洁的合成路线，通过碱诱导环转化4-sec-氨基-2-氧基-2,5-二氢噻唑烯[4,3-b]吡喃-3-氰基，与噻唑烯-4-酮、1-茚酮和2-茚酮单独反应，构建了外层螺旋上带有杂原子的噻烯基氧螺旋。P和4a的X射线研究显示，通过弱的C–H⋯O和C–H⋯N分子间相互作用形成超分子结构。在6a中观察到通过C–H⋯N和π⋯π的超分子链，而在7中则通过C–H⋯π和π⋯π的弱分子间相互作用。对Hirschfeld表面和指纹图的详细分析提供了一幅新合成化合物中非共价相互作用模式的比较图。利用DFT和AIM理论计算估算了与这些弱相互作用相关的稳定化能。