2-Mercapto-4-p-chlorophenyl-4H-1,2,3,4,5,6-hexahydrobenzo-quinazoline | 128483-26-1

• 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: 2-Mercapto-4-p-chlorophenyl-4H-1,2,3,4,5,6-hexahydrobenzo-quinazoline
• 英文别名: 4-(4-chlorophenyl)-3,4,5,6-tetrahydro-1H-benzo[h]quinazoline-2-thione；4-(4-chlorophenyl)-3,4,5,6-tetrahydrobenzo[h]quinazoline-2(1H)-thione；3,4,5,6-tetrahydro-4-(4-chlorophenyl)benzo[h]quinazoline-2(1H)thione；4-(4-chloro-phenyl)-3,4,5,6-tetrahydro-1H-benzo[h]quinazoline-2-thione；4-(4-Chlorophenyl)-3,4,5,6-tetrahydrobenzo[h]quinazoline-2-thiol
• CAS: 128483-26-1
• 化学式: C₁₈H₁₅ClN₂S
• 分子量: 326.849
• InChiKey: CEUVYLKUHIQWOL-UHFFFAOYSA-N

物化性质

• 熔点：
  252-254 °C(Solv: ethanol (64-17-5))
• 沸点：
  497.6±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Mercapto-4-p-chlorophenyl-4H-1,2,3,4,5,6-hexahydrobenzo-quinazoline 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 10-((1H-indol-3-yl)methylene)-7-(4-chlorophenyl)-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：

  E-2-(4-chlorobenzylidene)-1-tetralone 、 硫脲 在 zinc aluminate 作用下， 以 neat (no solvent) 为溶剂， 反应 3.0h， 以88%的产率得到2-Mercapto-4-p-chlorophenyl-4H-1,2,3,4,5,6-hexahydrobenzo-quinazoline
  参考文献：
  名称：

  ZnAl2O4纳米粉体上的HSBM技术绿色化学制备硫代色素[4,3-b]吡喃和苯并[h]噻唑并[2,3-b]喹唑啉衍生物。

  摘要：

  目的和目的本文的目的是介绍HSBM作为一种绿色环保技术，用于在ZnAl2O4纳米粉体上合成硫代色素[4,3-b]吡喃和苯并[h]噻唑并[2,3-b]喹唑啉衍生物作为有效的催化剂。材料与方法Zn（NO3）2和Al（NO3）3盐的共沉淀法合成了ZnAl2O4纳米粉，并通过XRD，FE-SEM，TEM和DLS技术对其进行了表征。所制备的ZnAl2O4纳米粉已被用作通过高速球磨（HSBM）技术合成吡喃核的催化剂。产物的结构通过NMR分析确认。结果ZnAl2O4呈现立方晶体结构（空间群：Fd-3m），平均晶粒尺寸为41 nm。通过DLS技术测定的ZnAl 2 O 4纳米粉末的平均粒径为55nm。研究了纳米粉体对2-氨基-4,5-二氢-4-芳基硫代色素[4,3-b]吡喃-3-腈，（8Z）-2-氨基-8-亚芳基的合成的催化活性。 -4,5，7,8-四氢-4-芳基硫代吡喃并[4,3-b]吡喃-3-腈，4-芳基-3

  DOI：

  10.2174/1386207322666190617164617

文献信息

• Synthesis, characterization and biological evaluation of fused thiazolo[3,2-a]pyrimidine derivatives
  作者：Janardhan Banothu、Manjulatha Khanapur、Srinivas Basavoju、Rajitha Bavantula、Muralikrishna Narra、Sadanandam Abbagani

  DOI：10.1039/c4ra02514h

  日期：——

  A series of fused thiazolo[3,2-a]pyrimidines (7a–g, 8a–f, 11a–g and 12a,b) have been synthesized in good yields by reaction of fused 3,4-dihydropyrimidin-2(1H)-thiones (4a–g) with phenacyl bromides (5,6)/3-(2-bromoacetyl)coumarins (9,10) under conventional heating in acetic acid. Analytical and spectral studies as well as single crystal X-ray diffraction data on the representative compound 8e confirmed

  通过融合3,4-二氢嘧啶-2（1 H）的反应以高收率合成了一系列稠合的噻唑并[3,2- a ]嘧啶（7a–g，8a–f，11a–g和12a，b）。）-thiones（4A-G ）与苯甲酰甲基溴化物（5，6）/ 3-（2-溴乙酰基）香豆素（9，10在乙酸常规加热下）。代表性化合物8e的分析和光谱研究以及单晶X射线衍射数据证实了所有反应产物的结构。筛选所有合成的化合物的抗菌，抗氧化剂和DNA裂解活性。与具有MIC 9.375μgmL -1的标准药物青霉素相比，抗大肠杆菌的化合物7e，抗铜绿假单胞菌的8a和8c–e具有显着的抗菌活性，而与MIC相比，化合物11c，12a和12b具有非常好的抗氧化活性。标准药物Trolox的IC 50值分别为12.36、11.12和13.88μM。化合物11f和12b甚至在50μgmL -1的浓度下也已完全切割了DNA ，其余化合物已部分切割了DNA。
• Benzo[h]thiazolo[2,3-b]quinazolines by an efficient p-toluenesulfonic acid-catalyzed one-pot two-step tandem reaction
  作者：B. Sakram、B. Sonyanaik、K. Ashok、S. Rambabu、S. K. Johnmiya

  DOI：10.1007/s11164-015-2112-4

  日期：2016.3

  A highly efficient method has been developed for synthesis of 7,9-disubstituted-6,7-dihydro-5H-benzo[h]thiazolo[2,3-b]quinazolines via multicomponent one-pot two-step tandem reaction involving 1-tetralone, arylaldehydes, thiourea, and 4-chlorophenacyl bromide/(3-bromoacetyl)coumarin utilizing p-toluenesulfonic acid as catalyst in glacial acetic acid under reflux conditions. Analytically pure products are formed with excellent yield and short reaction time. All the synthesized compounds were confirmed by their spectral and elemental analyses.

  一种高效的方法被开发用于合成7,9-二取代的6,7-二氢-5H-苯并[h]噻唑[2,3-b]喹唑啉，通过多组分一锅法两步串联反应，涉及1-四氢萘酮、芳基醛、硫脲和4-氯苯乙酰溴/（3-溴乙酰）香豆素，采用对甲苯磺酸作为催化剂，在冰醋酸下回流条件进行。通过这种方法形成的产品具有优良的纯度和高产率，同时反应时间短。所有合成化合物均通过光谱和元素分析进行了确认。
• 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。
• Efficient Ionic Liquid-Catalysed Synthesis and Antimicrobial Studies of 4,6-diaryl- and 4,5-fused pyrimidine-2-thiones
  作者：Richa Gupta、Ram Pal Chaudhary

  DOI：10.3184/174751912x13523931169712

  日期：2012.12

  One-pot three-component condensation of aromatic ketones (1-tetralones, acetophenones, indane-1,3-dione), substituted aromatic aldehydes and thiourea in the presence of N-methylpyridinium tosylate under solvent free conditions at 100–110 °C for 2–4 h afforded tetrahydrobenzo[ h]quinazoline-2-thiones, pyridimidine-2-thiones and indeno-pyrimidine-2-thiones in excellent yields. All synthesised thiones were screened for their antimicrobial activities.

  在 N-甲基吡啶鎓对甲苯磺酸盐存在下，在无溶剂条件下于 100-110 °C、2-4 h 内以单锅三组分缩合芳香酮（1-四氢酮、苯乙酮、茚-1,3-二酮）、取代芳香醛和硫脲，得到四氢苯并[h]喹唑啉-2-硫酮、吡啶-2-硫酮和茚并嘧啶-2-硫酮，产率极高。对所有合成的亚硫酰进行了抗菌活性筛选。
• Base-mediated one-pot synthesis of 3,4,5,6-tetrahydro-4-substituted benzo[<i>h</i>]quinazoline-2(1<i>H</i>)-thione derivatives and evaluation of their antioxidant activity
  作者：Matam Sivakumar、Kaliyan Prabakaran、Muthu Seenivasa Perumal

  DOI：10.1080/00397911.2017.1393688

  日期：2018.1.17

  ABSTRACT One-pot three-component Beginelli-like reactions of a ketone 1, an aryl aldehyde 2, and thiourea 3 in the presence of sodium hydroxide are described. In this reaction, 3,4,5,6-tertrahydro-4-substituted quinazoline-2(1H)-thione derivatives 4a–h were obtained in good yields (73–85%). The compound 4a has been characterized by single crystal X-ray analysis. All the synthesized compounds 4a–h and

  摘要描述了酮 1、芳基醛 2 和硫脲 3 在氢氧化钠存在下的一锅三组分类 Beginelli 反应。在该反应中，3,4,5,6-四氢-4-取代的喹唑啉-2(1H)-硫酮衍生物4a-h 以良好的产率（73-85%）获得。化合物 4a 已通过单晶 X 射线分析表征。筛选了所有合成的化合物 4a-h 和 5a-b 的体外抗氧化活性。化合物4c、4e和4h表现出优于标准抗坏血酸。化合物 4d、4f 和 4g 也显示出良好的活性。其余化合物显示中等抗氧化活性。图形概要