5-p-chlorophenyl-5H-2,3,6,7-tetrahydrobenzothiazolo<2,3-b>quinazoline-3-one | 128483-30-7

• 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: 5-p-chlorophenyl-5H-2,3,6,7-tetrahydrobenzothiazolo<2,3-b>quinazoline-3-one
• 英文别名: 7-(4-chlorophenyl)-5,7-dihydro-6H-10-thia-7a,11-diaza-cyclopenta[b]phenanthren-8-one；5-p-chlorophenyl-5H-2,3,6,7-tetrahydrobenzo[h]thiazolo[2,3-b]quinazoline-3-one；7-(4-Chlorophenyl)-10-thia-7a,11-diaza-6,7-dihydro-5H-cyclopenta[b]phenanthrene-8(9H)-one；11-(4-chlorophenyl)-15-thia-12,17-diazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,16-pentaen-13-one
• CAS: 128483-30-7
• 化学式: C₂₀H₁₅ClN₂OS
• 分子量: 366.871
• InChiKey: BKGPIZVLNPWNBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基吲哚-3-甲醛 、 5-p-chlorophenyl-5H-2,3,6,7-tetrahydrobenzothiazolo<2,3-b>quinazoline-3-one 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 3.5h， 以77%的产率得到7-(4-chlorophenyl)-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：

  2-(4-chlorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one 在 氢氧化钾 、 sodium acetate 、 乙酸酐 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 2.5h， 生成 5-p-chlorophenyl-5H-2,3,6,7-tetrahydrobenzothiazolo<2,3-b>quinazoline-3-one
  参考文献：
  名称：

  Hammam, Abou El-Fotooh G.; Hussain, S. M.; Kotob, Iman R., Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 47, # 1+2, p. 47 - 51

  摘要：

  DOI：

文献信息

• 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。
• Recyclable task-specific acidic ionic liquid [NMP]H2PO4: Microwave-assisted, efficient one-pot, two-step tandem synthesis of fused thiazolo[2,3-b]quinazolinone and thiazolo[2,3-b]quinazoline derivatives
  作者：Gondru Ramesh、Rajitha Gali、Ravibabu Velpula、Bavantula Rajitha

  DOI：10.1007/s11164-015-2249-1

  日期：2016.4

  A novel, time-effective, eco-conscious and microwave-assisted tandem one-pot, two-step reaction has been described for the synthesis of thiazolo[2,3-b]quinazolinone (4a–f) and thiazolo[2,3-b]quinazoline (5a–t) derivatives in quantitative yield in the presence of inexpensive, acidic task-specific ionic liquid [NMP]H2PO4. All the synthesized compounds were well established by comparison with their literature values (1H NMR, melting points, mass spectrometry and elemental analysis). The remarkable advantages of this methodology over existing conventional heating, such as increasing yields, decreasing reaction times, formation of products in an analytically pure form, operational simplicity, less energy consumption, cost-effectiveness, recyclability and reusability of the catalyst, make this protocol "green" and environmentally benign.

  在廉价的酸性特异性离子液体 [NMP]H2PO4 的存在下，描述了一种新颖、省时、环保和微波辅助的串联一锅两步反应，用于定量合成噻唑并[2,3-b]喹唑啉酮（4a-f）和噻唑并[2,3-b]喹唑啉（5a-t）衍生物。通过与文献值（1H NMR、熔点、质谱和元素分析）的比较，所有合成的化合物都得到了很好的证实。与现有的传统加热方法相比，该方法具有显著的优势，如产量增加、反应时间缩短、生成的产品分析纯度高、操作简单、能耗低、成本效益高、催化剂可回收和重复使用，因此该方法是 "绿色 "和环保的。
• Pal, Ram; Handa, R. N.; Pujari, H. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 7, p. 629 - 633
  作者：Pal, Ram、Handa, R. N.、Pujari, H. K.

  DOI：——

  日期：——
• 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.
• Hammam, Abou El-Fotooh G.; Hussain, S. M.; Kotob, Iman R., Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 47, # 1+2, p. 47 - 51
  作者：Hammam, Abou El-Fotooh G.、Hussain, S. M.、Kotob, Iman R.

  DOI：——

  日期：——