4-phenyl-2-thioxo-3,4-dihydro-1H-indeno[1,2-d]pyrimidin-5(2H)-one | 60477-74-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 4-phenyl-2-thioxo-3,4-dihydro-1H-indeno[1,2-d]pyrimidin-5(2H)-one
• 英文别名: 4-phenyl-2-thioxo-1,2,3,4-tetrahydro-5H-indeno[1,2-d]pyrimidin-5-one；4-phenyl-2-sulfanylidene-3,4-dihydro-1H-indeno[1,2-d]pyrimidin-5-one
• CAS: 60477-74-9
• 化学式: C₁₇H₁₂N₂OS
• 分子量: 292.361
• InChiKey: BGQSZBPWPOXQTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenyl-2-thioxo-3,4-dihydro-1H-indeno[1,2-d]pyrimidin-5(2H)-one 在 sodium acetate 、 乙酸酐 、 溶剂黄146 作用下， 反应 9.0h， 生成 2-benzylidene-5-phenylindeno[1,2-d]thiazolo[3,2-a]pyrimidine-3,6(2H,5H)-dione
  参考文献：
  名称：

  Synthesis, spectroscopic characterization and DFT studies on the novel indeno-thiazolopyrimidine heterocyclic system

  摘要：

  4-Phenyl-2-thioxo-3,4-dihydro-1H-indeno[1,2-d]pyrimidin-5(2H)-one 2, obtained by stirring a mixture of indane-1,3-dione, benzaldehyde and thiourea in acetic acid at room temperature for 12h, on reaction with chloroacetic acid and 1,2-dibromoethane furnish compounds 3 (or 6) and 4 (or 7), respectively. The regiochemistry of the cyclized products and their structure is established by an elemental analysis, H-1 NMR, C-13 NMR, IR and mass spectral data. Density functional theory calculations have been carried out for compounds 3 and 4 and their isomers 6 and 7 with Jaguar version 6.5112 using the B3LYP density functional method and LACVP* basis set. H-1 and C-13 NMR of compounds 3, 4, 6 and 7 have been calculated. 2-Arylidene derivatives of 3 were obtained by two routes and their structure was established by spectral data.

  DOI：

  10.1080/17415993.2013.801477
• 作为产物：
  描述：

  硫脲 、 2-(苯基亚甲基)茚-1,3-二酮 以60%的产率得到4-phenyl-2-thioxo-3,4-dihydro-1H-indeno[1,2-d]pyrimidin-5(2H)-one
  参考文献：
  名称：

  Salama, M. A.; Yousif, N. M.; Ahmed, F. H., Polish Journal of Chemistry, 1988, vol. 62, # 1-3, p. 243 - 250

  摘要：

  DOI：

文献信息

• Design, synthesis and bioevaluation of tricyclic fused ring system as dual binding site acetylcholinesterase inhibitors
  作者：Saba Tahir Tanoli、Muhammad Ramzan、Abbas Hassan、Abdul Sadiq、Muhammad Saeed Jan、Farhan A. Khan、Farhat Ullah、Haseen Ahmad、Maria Bibi、Tariq Mahmood、Umer Rashid

  DOI：10.1016/j.bioorg.2018.10.035

  日期：2019.3

  discovered non-classical acetylcholinesterase (AChE) function, dual binding-site AChE inhibitors have acquired a paramount attention of drug designing researchers. The unique structural arrangements of AChE peripheral anionic site (PAS) and catalytic site (CAS) joined by a narrow gorge, prompted us to design the inhibitors that can interact with dual binding sites of AChE. Eighteen homo- and heterodimers of

  由于最近发现了非经典的乙酰胆碱酯酶（AChE）功能，双重结合位点AChE抑制剂已引起药物设计研究人员的高度重视。AChE外围阴离子位点（PAS）和催化位点（CAS）的独特结构排列由狭窄的峡谷连接，促使我们设计可以与AChE的双重结合位点相互作用的抑制剂。合成了十八种去氯雷他定和咔唑的同二聚体和异二聚体（已可用的三环结构单元），并测试了它们对电鳗乙酰胆碱酯酶（eeAChE）和马血清丁酰胆碱酯酶（eqBChE）的抑制潜力。我们确定了基于地氯雷他定和茚二酮的三环二氢嘧啶（4c）的六碳系链异二聚体为eeAChE的有效和选择性抑制剂，IC50值为0.09±0。003μM和1.04±0.08μM（对于eqBChE），选择性指数为11.1。有效抑制剂的结合姿势分析表明，三环通过与Trp84和Trp279的疏水相互作用很好地容纳在AChE活性位点中。最具活性的异二聚体4b的茚满酮环稳定在峡谷底部，并与重要
• 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。
• Design, Synthesis, Characterization, and Antimicrobial Activity of Biginelli Products of Indandione
  作者：Vijay V. Dabholkar、Sunil R. Patil、Rajesh V. Pandey

  DOI：10.1002/jhet.860

  日期：2012.7

  method has been developed for the synthesis of 4‐(substituted phenyl)‐3,4‐dihydro‐1H‐indeno [1,2‐d] pyrimidine‐2,5‐dione (5) and 4‐(substituted phenyl)‐2‐thioxo‐1,2,3,4‐tetrahydroindeno [1,2‐d] pyrimidine‐5‐one (6), by a one‐pot three component cyclocondensation reaction of 1,3 dicarbonyl compound (Indandione) (1), aromatic aldehyde (2), and urea/thiourea (3/4) using catalytic amount of conc. HCl in

  已开发出一种简单有效的方法来合成4-（取代的苯基）-3,4-二氢-1H-茚并[1,2-d]嘧啶-2,5-二酮（5）和4-（取代的）（1），3-二羰基化合物（茚满二酮）的一锅三组分环缩合反应生成苯基）-2-硫代-2-2,3,4-四氢茚并[1,2-d]嘧啶-5- （6）（1），芳香醛（2）和尿素/硫脲（3/4），使用催化量的浓 在回流乙醇中的HCl。筛选代表性样品对革兰氏阴性菌，大肠杆菌和铜绿假单胞菌以及革兰氏阳性菌，金黄色葡萄球菌和白喉C杆菌的抗菌活性使用圆盘扩散法。产物的结构通过IR，1 H，13 C NMR和元素分析确认。
• COMPOUNDS USEFUL FOR TREATING INJURIES FROM WARFARE AGENTS
  申请人：Wu Xinyuan

  公开号：US20150352115A1

  公开（公告）日：2015-12-10

  Compounds and compositions for treating disorders related to TRPA1 are described herein.

  本文描述了用于治疗与TRPA1相关的疾病的化合物和组合物。
• 3-Aryl/Heteryl-5-Phenylindeno[1,2-d]thiazolo[3,2-a]pyrimidin-6(5H)-ones: Synthesis, Characterization, and Antimicrobial Investigation
  作者：G. Rajitha、C. G. Arya、B. Janardhan、S. V. Laxmi、G. Ramesh、U. Sujana Kumari

  DOI：10.1134/s106816202004007x

  日期：2020.7

  Discovery towards the potent antimicrobial agents is indispensable for the treatment of infections caused by resistant microbes. Thus, we prepared a novel series of 3-substituted 5-phenylindeno-thiazolopyrimidinone derivatives following conventional method. All the molecules were investigated for their in vitro antimicrobial potency against different bacteria and fungi, and the results were compared with streptomycin and clotrimazole standard drugs, respectively. Among the twelve analogs, 4-methoxyphenyl-5-phenylindeno[1,2-d]thiazolo[3,2-a]pyrimidin-6(5H)-one showed equipotent activity against a bacterium,Staphylococcus aureus(minimum inhibitory concentration 25 mu g/mL and zone of inhibition 22 mm), and a fungus,Aspergillus niger(zone of inhibition 20 mm). The rest of the thiazolo[3,2-a]pyrimidin-6(5H)-one derivatives exhibited week to reasonable activities against the tested bacterial and fungal strains.