7-(4-fluorophenyl)-3-methoxy-5,7-dihydro-6H-10-thia-7a,11-diaza-cyclopenta[b]phenanthren-8-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7-(4-fluorophenyl)-3-methoxy-5,7-dihydro-6H-10-thia-7a,11-diaza-cyclopenta[b]phenanthren-8-one
• 英文别名: 11-(4-Fluorophenyl)-5-methoxy-15-thia-12,17-diazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,16-pentaen-13-one；11-(4-fluorophenyl)-5-methoxy-15-thia-12,17-diazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,16-pentaen-13-one
• 化学式: C₂₁H₁₇FN₂O₂S
• 分子量: 380.443
• InChiKey: MKYQHIBTBCJNGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	4-(4-Fluorophenyl)-8-methoxy-3,4,5,6-tetrahydrobenzo[h]quinazoline-2-thiol	——	C19H17FN2OS	340.421

反应信息

• 作为反应物：
  描述：

  2-甲基吲哚-3-甲醛 、 7-(4-fluorophenyl)-3-methoxy-5,7-dihydro-6H-10-thia-7a,11-diaza-cyclopenta[b]phenanthren-8-one 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以82%的产率得到7-(4-fluorophenyl)-3-methoxy-10-((2-methyl-1H-indol-3-yl)methylene)-7,10-dihydro-5H-benzo[h]thiazolo[2,3-b]quinazolin-9(6H)-one
  参考文献：
  名称：

  Indolylmethylene benzo[h]thiazolo[2,3-b]quinazolinones: Synthesis, characterization and evaluation of anticancer and antimicrobial activities

  摘要：

  A series of novel 10-((1H-indol-3-yl)methylene)-7-aryl-7,10-dihydro-5H-benzo[h]thiazolo[2,3-b]quinazolin-9(6H)-ones (8a-t) have been synthesized in good yields by the reaction of benzo[h]quinazoline-2(1H)-thiones (4a-f) with 2-chloro-N-phenylacetamide (5) followed by Knoevenagel condensation with various indole-3-carbaldehydes (7a-d) under conventional method. All the synthesized compounds were characterized by spectral studies and screened for their in vitro anticancer and antimicrobial activities. Compound 8c has exhibited excellent activity against MCF-7 (breast cancer cell line) than the standard drug Doxorubicin. Compound 8d against both the cancer cell lines, 8q against MCF-7 and 8c, 8h against HepG2 have also shown good activity. Remaining compounds have shown moderate activity against both the cell lines. Antimicrobial activity revealed that, the compound 8q and 8t against Staphylococcus aureus and 8i, 8k, 8l, 8q &8t against Klebsiella pneumoniae have shown equipotent activity on comparing with the standard drug Streptomycin. Remaining compounds have shown significant antibacterial and comparable antifungal activities against all the tested microorganisms.

  DOI：

  10.1016/j.bmcl.2014.07.030
• 作为产物：
  描述：

  对氟苯甲醛 在 sodium acetate 、 溶剂黄146 作用下， 以 neat (no solvent) 为溶剂， 反应 4.0h， 生成 7-(4-fluorophenyl)-3-methoxy-5,7-dihydro-6H-10-thia-7a,11-diaza-cyclopenta[b]phenanthren-8-one
  参考文献：
  名称：

  稠合噻唑并[3,2- a ]嘧啶酮的合成：N-芳基-2-氯乙酰胺为双亲电子结构单元

  摘要：

  2-氯-N-苯基乙酰胺和N-（苯并[ d ]噻唑-2-基）-2-氯乙酰胺是形成环环化的噻唑并[3,2- a ]嘧啶酮产物的双亲电结构单元。该合成途径涉及通过消除副产物苯胺/ 2-氨基苯并噻唑而以可接受的产物收率形成标题化合物。对代表性化合物6c的分析和光谱研究以及单晶X射线数据证实了所有反应产物的结构。

  DOI：

  10.1016/j.tetlet.2013.11.001

文献信息

• Indolylmethylene benzo[h]thiazolo[2,3-b]quinazolinones: Synthesis, characterization and evaluation of anticancer and antimicrobial activities
  作者：Rajitha Gali、Janardhan Banothu、Mahendar Porika、Ravibabu Velpula、Sairengpuii Hnamte、Rajitha Bavantula、Sadanandam Abbagani、Siddhardha Busi

  DOI：10.1016/j.bmcl.2014.07.030

  日期：2014.9

  A series of novel 10-((1H-indol-3-yl)methylene)-7-aryl-7,10-dihydro-5H-benzo[h]thiazolo[2,3-b]quinazolin-9(6H)-ones (8a-t) have been synthesized in good yields by the reaction of benzo[h]quinazoline-2(1H)-thiones (4a-f) with 2-chloro-N-phenylacetamide (5) followed by Knoevenagel condensation with various indole-3-carbaldehydes (7a-d) under conventional method. All the synthesized compounds were characterized by spectral studies and screened for their in vitro anticancer and antimicrobial activities. Compound 8c has exhibited excellent activity against MCF-7 (breast cancer cell line) than the standard drug Doxorubicin. Compound 8d against both the cancer cell lines, 8q against MCF-7 and 8c, 8h against HepG2 have also shown good activity. Remaining compounds have shown moderate activity against both the cell lines. Antimicrobial activity revealed that, the compound 8q and 8t against Staphylococcus aureus and 8i, 8k, 8l, 8q &8t against Klebsiella pneumoniae have shown equipotent activity on comparing with the standard drug Streptomycin. Remaining compounds have shown significant antibacterial and comparable antifungal activities against all the tested microorganisms.
• Synthesis of fused thiazolo[3,2-a]pyrimidinones: N-aryl-2-chloroacetamides as doubly electrophilic building blocks
  作者：Banothu Janardhan、Basavoju Srinivas、Bavantula Rajitha、Crooks Peter A.

  DOI：10.1016/j.tetlet.2013.11.001

  日期：2014.1

  2-Chloro-N-phenylacetamide and N-(benzo[d]thiazol-2-yl)-2-chloroacetamide are doubly electrophilic building blocks for the formation of ring annulated thiazolo[3,2-a]pyrimidinone products. This synthetic route involves formation of the title compound in acceptable product yields by the elimination of the by-product, aniline/2-aminobenzothiazole. Analytical and spectral studies, as well as single crystal

  2-氯-N-苯基乙酰胺和N-（苯并[ d ]噻唑-2-基）-2-氯乙酰胺是形成环环化的噻唑并[3,2- a ]嘧啶酮产物的双亲电结构单元。该合成途径涉及通过消除副产物苯胺/ 2-氨基苯并噻唑而以可接受的产物收率形成标题化合物。对代表性化合物6c的分析和光谱研究以及单晶X射线数据证实了所有反应产物的结构。