- Synthesis and evaluation of anticancer and PDE 5 inhibitory activity of spiro-substituted quinazolin-4-ones
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A series of novel spiro-substituted 2,3-dihydroquinazolin-4(1H)-ones was synthesized and structurally confirmed by spectral analysis, screened for their anticancer activity at a concentration of 10 μΜ against a panel of 56 cell lines derived from nine different types of cancers, including leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers. The synthesized compounds screened for their PDE 5 inhibitory activity and it showed encouraged activity compared to sildenafil. Graphical abstract: [Figure not available: see fulltext.].
- Ameen, Mohamed A.,Ahmed, Essam Kh.,Ramadan, Mohamed,Abd El-Naby, Hisham A.,Abdel-Haseeb, Asmaa A.
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p. 1513 - 1523
(2017/07/18)
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- Design, synthesis and biological evaluation of novel quinazoline-based anti-inflammatory agents acting as PDE4B inhibitors
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A novel series of quinzoline based compounds (IIIa-d, VIa-f, IXa-f) were designed, synthesized and screened for their inhibitory activity towards the PDE4B isoform. The in vivo anti-inflammatory effect of the titled compounds (IIIa-d, VIa-f, IXa-f) as well as their effect on the level of tumor necrosis factor (TNF-α) were evaluated. Among all of the synthesized compounds, IXb, IXd and IXf, exhibited good inhibitory activity against PDE4B enzyme with inhibition percentages of 42, 62 and 68%, respectively. Most of the tested compounds showed potent anti-inflammatory activity compared to indomethacin with a marked decrease in TNF-α level. The ulcerogenic effect of the tested compounds was also examined. The gastric mucosa of the tested animals remained intact after oral administration of the hit compounds. Additionally, docking study was used to explore the possible binding mode of the active compounds on the PDE4B enzyme as well as to illustrate the selectivity of the active hits on the PDE4B isoform.
- Serya, Rabah Ahmed Taha,Abbas, Abeer Hussin,Ismail, Nasser Saad Mohamed,Esmat, Ahmed,El Ella, Dalal Abdelrahman Abou
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p. 102 - 116
(2015/02/19)
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- Synthesis of benzoxazolthiolyl and benzthiazolthiolyl fused 3- alkylquinazolin-4(3H)-ones
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Condensation of anthranilamide (1) with chloroacetyl chloride for 1 hr at RT gave 2- (2-chloroacetamido) benzamide (2). The latter, on refluxation in acetic acid for 2 hr gave 2-(chloromethyl) quinazolin-4(3H)-one (3). Condensation of 3, independently, with each one of benz [d] oxazole-2-thiol (4a) and benz [d] thiazole-2-thiol (4b), for 3-4 hr, gave 2-((benz [d] oxazol-2-ylthio) methyl) quinazolin-4(3H)-one (5a) and 2-((benz [d] thiazol-2-ylthio) methyl) quinazolin-4(3H)-one (5b) respectively. Each one of the 5a and 5b, independently and selectively, when treated with alkylating agents (i.e. DMS, DES, PhCH2Cl), gave 2-((benz [d] oxazol-2-ylthio) methyl)-3-alkylquinazolin-4(3H)-ones (6a-c) and 2-((benz [d] thiazol-2-ylthio) methyl)-3-alkylquinazolin-4(3H)-ones (6d-f) respectively. The latter 6a-f could also be prepared, alternatively, by condensing chloromethyl-3-alkylquinazolin-4(3H)-one (7a-c) with 4a-b respectively, in good yields.
- Rafeeq, Md.,Reddy, Ch. Venkata Ramana,Dubey
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p. 405 - 410
(2019/01/21)
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- PYRAZOLE AMIDE COMPOUND AND USE THEREOF
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Disclosed is a pyrazole amide compound having fungicidal activity, with a structure shown by the general formula (I): Each of the substituents of the compound being defined as in the description. The compound of the present invention has fungicidal activity, and excellent prevention and controlling effects on diseases, such as cucumber downy mildew, corn rust, wheat powdery mildew, rice blast, etc., and in particular, a better prevention and controlling effect on cucumber downy mildew and corn rust. Also disclosed is a process for preparing the compound, a fungicidal composition containing the compound of general formula(I) and the use thereof in preventing and controlling disease in crops.
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Paragraph 0130; 0094; 0129
(2013/09/26)
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- Synthesis of novel 2-(4-oxo-3,4-dihydroquinazolin-2-ylsulfinylmethyl)-3H- quinazolin-4-one
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Condensation of 2-mercapto-3H-quinazolin-4-one (1) with chloroacetic acid gave 4-oxo-3,4-dihydroquinazoline-2-yl-sulfanyl)-acetic acid (2) that with anthranilamide (3) gave 2-(4-oxo-3,4-dihydroquinazolin-2-ylsulfanylmethyl)-3H- quinazolin-4-one (4). Oxidation of 4 with sodium hypochlorite in alkaline medium gave the novel product, 2-(4-oxo-3,4-dihydroquinazolin-2-ylsulfinyl methyl)-3H-quinazolin-4-one) (5). The entire sequences of reactions in this work have been carried out using eco-friendly solvents and green conditions. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
- Reddy, B. Srinivasa,Naidu,Dubey
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scheme or table
p. 598 - 605
(2012/06/18)
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- Novel glitazones: Glucose uptake and cytotoxic activities, and structure-activity relationships
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In this article, two series of novel glitazones are reported for their synthesis, in vitro glucose uptake activity by the rat hemi-diaphragm, and in vitro cytotoxic activity against human carcinoma HEp-2 (epidermoid carcinoma of the larynx) and A549 (human lung cancer cell line) cells. Some of the compounds exhibit good glucose uptake and cytotoxic activities. Compound 5 with 2,4-dichlorophenol moiety connected to TZD via the two carbon linker has exhibited good glucose uptake activity. One of the compounds exhibits both cytotoxic and glucose uptake activities (compound 4). Illustrations about their synthesis, and in vitro glucose uptake and cytotoxic activities are described along with their structure-activity relationships.
- Kumar, B. R. Prashantha,Kumar, S. Santhosh,Viral, Patel,Wadhwani, Ashish,Vadivelan, R.,Kumar, M. N. Satish,Elango, K.,Nanjan, M. J.
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p. 2689 - 2701,13
(2020/07/30)
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- Molecular modeling study and synthesis of quinazolinone-arylpiperazine derivatives as α1-adrenoreceptor antagonists
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Three series of new 2-[(4-substituted piperazin-1-yl) methyl]quinazolin- 4(3H)-ones 4a-c, Ethyl 6,7-dimethoxy-4-oxo-3-[2-(4-substituted piperazin-1-yl)acetamido/propanamido]-3,4-dihydroquinazoline-2-carboxylates 9a-f and their 2-methyl analogues 13a-l were designed and synthesized as promising α1-adrenoceptor antagonists. The final compounds were evaluated for their in vivo hypotensive activity in normotensive cats. The most potent hypotensive quinazolinone derivatives 4b, 9e, 13i, 13j were further tested on isolated thoracic aortic rings of male Wister rats. All the tested compounds displayed α1-blocking activity with IC50 ranging from 0.2 to 0.4 mM less than prazosin. Furthermore, in the present work, molecular modeling study using Accelrys Discovery Studio 2.1 software was performed by mapping the synthesized compounds to the α1- adrenoceptor antagonist hypothesis in order to predict their mechanism of action. Compound 13j which has the best-fitting score displayed the highest in vivo and in vitro activity among the tested compounds.
- Abou-Seri, Sahar Mahmoud,Abouzid, Khaled,Abou El Ella, Dalal A.
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scheme or table
p. 647 - 658
(2011/03/22)
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- Novel glitazones: Design, synthesis, glucose uptake and structure-activity relationships
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Glitazones are known to exhibit antihyperglycemic activity by decreasing peripheral insulin resistance. In the present study, we have designed some novel glitazones based on the structure-activity relationships as possible PPAR-γ agonists. The manually designed glitazones were synthesized by using the appropriate synthetic schemes and screened for their in vitro antihyperglycemic activity by estimating glucose uptake by rat hemi-diaphragm, both in the absence and in the presence of external insulin. Some of the glitazones exhibited good antihyperglycemic activity in presence of insulin. Illustration about their design, synthesis, evaluation, and structure-activity relationships is described.
- Kumar, B.R. Prashantha,Nanjan
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scheme or table
p. 1953 - 1956
(2010/07/02)
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- Synthesis of original 2-substituted 4-arylquinazolines by microwaveirradiated Suzuki-Miyaura cross-coupling reactions
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Original 2-substituted 4-arylquinazollnes have been synthesized by using a microwave-assisted Suzuki-Miyaura crosscoupling approach, The optimization and generalization of the Suzuki-Miyaura cross-coupling reaction between 2-sub-stituted 4-chloroquinazolines and various boronlc acids are described herein,
- Kabri, Youssef,Gellis, Armand,Vanelle, Patrice
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scheme or table
p. 4059 - 4066
(2009/12/24)
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- Microwave-assisted synthesis in aqueous medium of new quinazoline derivatives as anticancer agent precursors
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Fast and eco-friendly microwave-irradiated reactions permitting the "green synthesis" of new 2-substituted quinazoline derivatives in aqueous medium via S-alkylation or SRN1 reaction from 2-chloromethyl-3-methylquinazolin-4(3H)-one derivatives with different benzenesulfinic acids and nitronate anions, are reported herein.
- Kabri,Gellis,Vanelle
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experimental part
p. 201 - 208
(2010/04/22)
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- 4-heteryl-β-lactams : A facile synthesis of 1-aryl-4- [isopropylideneamino/methyl-4(3H)-oxoquinazolin-2-yl] azetidin-2-ones
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A facile and efficient synthesis of 4-quinazolinonyl-β-lactams 9 and 10 starting from 2-chloromethylquinazolin-4(3H)-ones 1 is reported.
- Reddy,Vasantha,Naga Raju
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- A new synthesis of 2-aryl-2H-pyrazino[2,1-b]quinazolin-3,6(1H,4H)-diones
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A new synthesis of 2-aryl-2H-pyrazino [2,1-b]quinazolin-3,6(1H,4H)-diones starting from 2-chloromethylquinazolin-4(3H)-one is described.
- Reddy,Nagaraju Ch.
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p. 173 - 181
(2007/10/02)
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