3,4,5,6-tetrahydro-8-methoxy-4-(3-nitrophenyl)benzo[h]quinazolin-2-(1H)-thione | 313968-42-2

• 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: 3,4,5,6-tetrahydro-8-methoxy-4-(3-nitrophenyl)benzo[h]quinazolin-2-(1H)-thione
• 英文别名: 8-methoxy-4-(3-nitrophenyl)-3,4,5,6-tetrahydrobenzo[h]quinazoline-2(1H)-thione；8-methoxy-4-(3-nitrophenyl)-3,4,5,6-tetrahydro-1H-benzo[h]quinazoline-2-thione
• CAS: 313968-42-2
• 化学式: C₁₉H₁₇N₃O₃S
• 分子量: 367.428
• InChiKey: STFIYRVRCCJXBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 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：
  111
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4,5,6-tetrahydro-8-methoxy-4-(3-nitrophenyl)benzo[h]quinazolin-2-(1H)-thione 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 10-((1H-indol-3-yl)methylene)-3-methoxy-7-(3-nitrophenyl)-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：

  间硝基苯甲醛 、 硫脲 、 6-甲氧基-1-萘满酮 在 (4-sulfobutyl)-tris(4-sulfophenyl)phosphonium hydrogen sulfate 作用下， 反应 0.33h， 以90%的产率得到3,4,5,6-tetrahydro-8-methoxy-4-(3-nitrophenyl)benzo[h]quinazolin-2-(1H)-thione
  参考文献：
  名称：

  使用新型离子液体作为有效且可重复使用的催化剂，一锅合成稠合 3,4-二氢嘧啶-2(1H)-酮和硫酮：改进 Biginelli 样支架的方案条件

  摘要：

  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。

  DOI：

  10.1515/hc-2011-0109

文献信息

• 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。
• 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.
• 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。