4-(4-Fluorophenyl)-8-methoxy-3,4,5,6-tetrahydrobenzo[h]quinazoline-2-thiol

• 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: 4-(4-Fluorophenyl)-8-methoxy-3,4,5,6-tetrahydrobenzo[h]quinazoline-2-thiol
• 英文别名: 4-(4-fluorophenyl)-8-methoxy-3,4,5,6-tetrahydro-1H-benzo[h]quinazoline-2-thione
• 化学式: C₁₉H₁₇FN₂OS
• 分子量: 340.421
• InChiKey: PUKPSVVFUXDPDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  65.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-Fluorophenyl)-8-methoxy-3,4,5,6-tetrahydrobenzo[h]quinazoline-2-thiol 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 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 、 硫脲 、 6-甲氧基-1-萘满酮 在 poly(4-vinylpyridinium)hydrogen sulfate 作用下， 以 neat (no solvent) 为溶剂， 生成 4-(4-Fluorophenyl)-8-methoxy-3,4,5,6-tetrahydrobenzo[h]quinazoline-2-thiol
  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

• One-pot and solvent-free synthesis of 3-(9-hydroxy-3-methoxy-7-aryl-6,7,9,10-tetrahydro-5$H$-benzo[$h$]thiazolo[2,3-$b$]quinazolin-9-yl)-2$H$-chromen-2-ones and their antibacterial evaluation
  作者：Ravibabu VELPULA、Janardhan BANOTHU、Rajitha GALI、Yakaiah SARGAM、Rajitha BAVANTULA

  DOI：10.3906/kim-1410-64

  日期：——

  A series of 3-(9-hydroxy-3-methoxy-7-aryl-6,7,9,10-tetrahydro-5$H$-benzo[$h$]thiazolo[2,3-$b$]quinazolin-9-yl)-2$H$-chromen-2-ones (5a-j) were synthesized by one-pot multicomponent reaction of 6-methoxy-1-tetralone, aryl aldehydes, and thiourea followed by cyclization with 3-(2-bromoacetyl)-2$H$-chromen-2-one in the presence of a Bronsted solid acid catalyst, poly(4-vinylpyridinium)hydrogen sulfate [P(4-VPH)HSO$_4}$] (0.015 g), under solvent-free conditions at 120 $^\circ}$C. All the synthesized compounds were characterized by spectral studies and screened for their in vitro antibacterial activity against S. aureus and B. thuringiensis (gram positive), and E. coli and K. pneumoniae (gram negative) bacterial strains. On comparing with the standard drug gentamicin, compounds derived from 4-methoxy and 3,4,5-trimethoxy benzaldehyde, i.e. 5g and 5h, showed broad spectrum antibacterial activity and the remaining compounds showed weak to moderate activity.

  合成了一系列3-(9-羟基-3-甲氧基-7-芳基-6,7,9,10-四氢-5$H$-苯并[$h$]噻唑[2,3-$b$]喹唑啉-9-基)-2$H$-香豆素-2-酮 (5a-j)，该反应通过在无溶剂条件下，使用布朗斯特固体酸催化剂聚(4-乙烯基吡idine)氢硫酸盐[P(4-VPH)HSO$_4}$] (0.015 g) 在120 $^\circ}$C下进行多组分一锅反应，反应物包括6-甲氧基-1-四氢烯酮、芳醛和硫脲，随后与3-(2-溴乙酰)-2$H$-香豆素-2-酮环化。所有合成的化合物通过光谱研究进行表征，并对其在体外抗菌活性进行了筛选，抗击金黄色葡萄球菌和巴氏嗜麦芽糖菌（革兰氏阳性菌），以及大肠杆菌和克雷伯氏肺炎菌（革兰氏阴性菌）菌株。与标准药物庆大霉素相比，从4-甲氧基和3,4,5-三甲氧基苯甲醛衍生的化合物，即5g和5h显示出广谱抗菌活性，其他化合物则表现出弱到中等的活性。
• One-pot synthesis, biological evaluation and molecular docking studies of fused thiazolo[2,3-b]pyrimidinone-pyrazolylcoumarin hybrids
  作者：Ramesh Gondru、Saikiran Reddy Peddi、Vijjulatha Manga、Manjulatha Khanapur、Rajitha Gali、Narsimha Sirassu、Rajitha Bavantula

  DOI：10.1007/s11030-018-9845-0

  日期：2018.11

  AbstractAs a part of our endeavor toward the synthesis of a new class of biologically potent heterocyclic hybrids, a series of newly fused thiazolo[2,3-b]pyrimidinones bearing a pyrazolylcoumarin moiety (6a–p) were synthesized in acceptable yields. Anticipated structures of all titled compounds were in agreement with spectral and analytical (C, H and N) analyses. The compounds were screened for in

  摘要作为我们合成一类新的具有生物活性的杂环杂种的努力的一部分，以可接受的产率合成了一系列带有吡唑基香豆素部分（6a – p）的新融合的噻唑并[2,3- b ]嘧啶酮。所有标题化合物的预期结构与光谱和分析（C，H和N）分析相符。化合物进行了筛选的体外抗菌活性对两种ģ +和G -细菌菌株和针对K562（慢性粒细胞性白血病），MCF-7（乳腺癌），MDA-MB-231（乳腺癌），COLO 205（结肠直肠腺癌），HepG2（肝细胞癌）细胞系的抗增殖活性。此外，对强效抗菌化合物进行了分子对接研究，以便深入了解其合理的结合模式和针对MurB的作用机理。建模结果与实验数据吻合。 图形概要
• 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。