8-methoxy-4-(4-methoxyphenyl)-3,4,5,6-tetrahydrobenzo[h]quinazoline-2(1H)-thione | 313968-32-0

• 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: 8-methoxy-4-(4-methoxyphenyl)-3,4,5,6-tetrahydrobenzo[h]quinazoline-2(1H)-thione
• 英文别名: 3,4,5,6-tetrahydro-8-methoxy-4-(4-methoxyphenyl)benzo[h]quinazolin-2-(1H)-thione；8-Methoxy-4-(4-methoxyphenyl)-3,4,5,6-tetrahydrobenzo[h]quinazoline-2-thiol；8-methoxy-4-(4-methoxyphenyl)-3,4,5,6-tetrahydro-1H-benzo[h]quinazoline-2-thione
• CAS: 313968-32-0
• 化学式: C₂₀H₂₀N₂O₂S
• 分子量: 352.457
• InChiKey: UNPWDRKHVWKMAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-methoxy-4-(4-methoxyphenyl)-3,4,5,6-tetrahydrobenzo[h]quinazoline-2(1H)-thione 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 10-((1H-indol-3-yl)methylene)-3-methoxy-7-(4-methoxyphenyl)-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：

  4-甲氧基苯甲醛 在 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 36.0h， 生成 8-methoxy-4-(4-methoxyphenyl)-3,4,5,6-tetrahydrobenzo[h]quinazoline-2(1H)-thione
  参考文献：
  名称：

  一些融合的吲唑，喹唑啉和喹啉作为潜在的EGFR抑制剂的合成及体外抗癌评估。

  摘要：

  由6-甲氧基-3合成苯并[g]吲唑5a，b，苯并[h]喹唑啉7、12a-c，13a-c和15a-c的衍生物以及苯并[h]喹啉17a-c和19a-c。 ，4-二氢萘-1（2H）-一（1）。评估了所有合成化合物对四种癌细胞的抗癌活性。HepG2，MCF-7，HCT116和Caco-2。MCF-7细胞作为对目标化合物最敏感的细胞系出现。除5a和5b外，所有受检化合物均显示出对MCF-7细胞有效的中度抗癌活性，IC50值为7.21至21.55 µM。特别是，化合物15c和19b成为表达EGFR的MCF-7细胞最有效的衍生物，IC50值分别为7.70±0.39和7.21±0.43μM。此外，两种化合物对正常的BHK-21成纤维细胞均无任何明显的细胞毒性（IC50值> 200 µM），因此作为抗癌剂具有良好的安全性。此外，与厄洛替尼（IC50 = 0.11±0.01μM）相比，化合物15c和19b在亚微摩尔范围内（分别为IC50

  DOI：

  10.1016/j.bioorg.2019.102985

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 of fused 3,4-dihydropyrimidin-2(1<i>H</i>)-ones and thiones using a novel ionic liquid as an efficient and reusable catalyst: improved protocol conditions for the Biginelli-like scaffolds
  作者：Banothu Janardhan、Somarapu Vijaya Laxmi、Bavanthu Rajitha

  DOI：10.1515/hc-2011-0109

  日期：2012.4.1

  Abstract A novel ionic liquid with multi-SO3H groups has been found to be an efficient acid catalyst for the one-pot three-component synthesis of fused 3,4-dihydropyrimidin-2(1H)-ones and thiones under solvent free conditions. Good yields, short reaction times, straight forward workup, reusability of the catalyst and green conditions are the most obvious advantages of this methodology.

  摘要 一种具有多 SO3H 基团的新型离子液体已被发现是一种有效的酸催化剂，可用于在无溶剂条件下一锅三组分合成稠合 3,4-二氢嘧啶-2(1H)-酮和硫酮。良好的收率、较短的反应时间、直接的后处理、催化剂的可重复使用性和绿色条件是该方法最明显的优势。
• 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 and in vitro anticancer evaluation of some fused indazoles, quinazolines and quinolines as potential EGFR inhibitors
  作者：Esraa A. Abdelsalam、Wafaa A. Zaghary、Kamilia M. Amin、Nageh A. Abou Taleb、Amal A.I. Mekawey、Wagdy M. Eldehna、Hatem A. Abdel-Aziz、Sherif F. Hammad

  DOI：10.1016/j.bioorg.2019.102985

  日期：2019.8

  derivatives of benzo[g]indazole 5a, b, benzo[h]quinazoline 7, 12a-c, 13a-c and 15a-c and benzo[h]quinoline 17a-c and 19a-c were synthesized from 6-methoxy-3,4-dihydronaphthalen-1(2H)-one (1). Anticancer activity of all the synthesized compounds was evaluated against four cancerous cell lines; HepG2, MCF-7, HCT116 and Caco-2. MCF-7 cells emerged as the most sensitive cell line against the target compounds

  由6-甲氧基-3合成苯并[g]吲唑5a，b，苯并[h]喹唑啉7、12a-c，13a-c和15a-c的衍生物以及苯并[h]喹啉17a-c和19a-c。 ，4-二氢萘-1（2H）-一（1）。评估了所有合成化合物对四种癌细胞的抗癌活性。HepG2，MCF-7，HCT116和Caco-2。MCF-7细胞作为对目标化合物最敏感的细胞系出现。除5a和5b外，所有受检化合物均显示出对MCF-7细胞有效的中度抗癌活性，IC50值为7.21至21.55 µM。特别是，化合物15c和19b成为表达EGFR的MCF-7细胞最有效的衍生物，IC50值分别为7.70±0.39和7.21±0.43μM。此外，两种化合物对正常的BHK-21成纤维细胞均无任何明显的细胞毒性（IC50值> 200 µM），因此作为抗癌剂具有良好的安全性。此外，与厄洛替尼（IC50 = 0.11±0.01μM）相比，化合物15c和19b在亚微摩尔范围内（分别为IC50