65331-17-1Relevant academic research and scientific papers
Design, synthesis and biological evaluation of novel dihydropyrimidine-2-thione derivatives as potent antimicrobial agents: Experimental and molecular docking approach
Mughal, Ehsan Ullah,Sadiq, Amina,Hamayun, Muhammad,Zafar, Muhammad Naveed,Fatima, Nighat,Yameen, Muhammad Arfat,Muhammad, Syed Aun,Mumtaz, Amara,Ahmed, Ishtiaq,Fatima, Tehseen
, p. 1189 - 1201 (2018/11/01)
Introduction: Dihydropyrimidine scaffold represent an important class of pharmacologically active nitrogen containing heterocyclic compounds. A wide range of molecules with dihydropyrimidine moieties have important role in medicinal chemistry on account of their potential biological activities. Methodology: A series of 3,4-dihydropyrimidine-2(1H)-thione derivatives have been designed and synthesized in a concise way through condensation of variously substituted chalcones with thiourea in alkaline alcoholic solutions. In order to investigate their biological significance, these compounds were tested for their in vitro antimicrobial potential against various bacterial and fungal strains. Moreover, the experimental results were supported by molecular docking studies. Results and Discussion: The newly synthesized compounds were characterized by the usual spectroscopic techniques In case of antibacterial activity, the compounds 5 (40.3±0.44 mm), 12 and 13 (almost 35 mm) exhibited highest zone of inhibitions against Methicillin-resistant Staphylococcus auerus (MRSA) bacterial strain as compared to the standard drug Cefixime. These compounds displayed moderate to good activities against all attempted fungal strains. In docking analysis, it has been observed that compounds 8 (-6.4017 Kcal/mol) and 10 (-6.1319 Kcal/mol) revealed significant binding affinity against penicillin binding protein (PDB ID: 1VQQ), while compounds 1 (-143.23 Kcal/mol) and 2 (-146.99 Kcal/mol) showed best activity for shikimate dehydrogenase (PDB ID: 3DON). Conclusion: In conclusion, we have designed, synthesized and characterized an interesting series of biologically active dihydropyrimidine derivatives. Remarkably, most of the synthesized compounds were found more active against all tested bacterial strains in comparison to the standard drug Cefixime as manifested by experimental as well as theoretical results.
Synthesis and biological activities of some new C-Aminomethylation of 5H-5-Aryl-6,7,8,9-tetrahydrothiazolo[2,3-b]quinazolin-3(2H)-one and 6H-6-Aryl-2,3,7,8,9,10-hexahydrothiazino[2,3-b]quinazolin-4(3H)-one
Kumaraswamy, Damerakonda,Mallareddy
, p. 2231 - 2235 (2016/07/21)
The synthesis of 5H-5-aryl-6,7,8,9-tetrahydrothiazolo[2,3-b]quinazolin-3(2H)-one and 6H-6-aryl-2,3,7,8,9,10-hexahydrothiazino[2,3-b]quinazolin-4(3H)-one, reaction between 4-aryl-3,4,5,6,7,8-hexahydroquinazolin-2-thione and methyl chloroacetate and ethyl β-bromo propionate. The Mannich reaction on 5H-5-aryl-6,7,8,9-tetrahydrothiazolo[2,3-b]quinazolin-3(2H)-one and 6H-6-aryl-2,3,7,8,9,10-hexahydrothiazino[2,3-b]quinazolin-4(3H)-one in ethanol, aqueous formaldehyde and different secondary amines yielded a single product C-Mannich base in each case. The obtained C-Mannich bases (compounds VIII and X) have been characterized on the basis of analytical spectral data. These C-Mannich bases have been screened for their antibacterial, antifungal, anti-inflammatory and analgesic activities.
Synthesis of new pyrimidine, quinazoline and diazatricyclo derivatives by multicomponent reaction and evaluation of their biological activity
Mobinikhaledi, Akbar,Foroughifar, Naser,Mosleh, Tahere,Hamta, Ahmad
experimental part, p. 728 - 734 (2012/06/18)
A series of new pyrimidine and quinazoline derivatives was synthesized by a Biginelli-like reaction of urea/thiourea, aldehyde, and ketone in the presence of hydrochloric acid as a catalyst. In a similar way, some novel diazatricyclo derivatives were obtained via a Biginelli-like reaction followed by an intramolecular Michael-type addition. The yields of products were reasonable after recrystallization from ethanol. All newly synthesized compounds were characterized using IR and NMR (1H and 13C) spectroscopy and elemental analysis. The antibacterial activity of these compounds was investigated against Staphylococcus aureus (RTCC, 1885), and Escherichia Coli (ATCC, 35922). 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. Copyright
Synthesis of 3,4-dihydropyrimidin-2(1H)ones and 3,4,5,6,7,8- hexahydroquinazolin-2(1H)-ones via three component cyclocondensation
Phucho,Nongpiur,Nongrum,Nongkhlaw
experimental part, p. 346 - 350 (2010/10/03)
3,4 Dihydropyrimidin-2(1H)-ones and 3,4,5,6,7,8-hexahydroquinazolin-2(1H)- ones have been synthesized from the condensation of ketones, aldehydes and urea/thiourea in the presence of sodium tertiary butoxide by the solventless microwave irradiation (MWI)
Development of new molecular entities as potent non-steroidal non-acidic anti-inflammatory agents - Part-I: Synthesis of some substituted pyrazolo-[3,4-a] thiozolo [2′,3'-b] quinazolines
Akula, Kalyan Chakravarthy,Tatikonda, Suresh,Reddy Vanga, Malla
, p. 389 - 394 (2007/10/03)
Eight 6-aryl-2,3,4,5-tetrahydro-7,8,9,10-tetrahydro-11H-pyrazolo [3,4-a] thiazolo [2,3-b] quinazolines were prepared 5a-h from the respective 5H-5-aryl-6,7,8,9-tetrahydro thiazolo[2,3-b]quinazolin-3(2H)-ones by a cycloaddition reaction of hydrazine/phenyl
Highly chemoselective multicomponent biginelli-type condensations of cycloalkanones, urea or thiourea and aldehydes
Zhu, Yu-Lin,Huang, Shen-Lin,Pan, Yuan-Jiang
, p. 2354 - 2367 (2007/10/03)
The classical Biginelli reaction is considerably extended by use of cycloalkanones instead of 1,3-dicarbonyl compounds. Use of TMSCl as a Lewis acid allowed one-pot chemoselective multicomponent Biginelli reactions between cycloalkanones, urea or thiourea, and aldehydes. Under similar reaction conditions, thiourea exhibited different behavior to urea, and aliphatic aldehydes showed lower reactivity than aromatic aldehydes. A possible mechanism to account for the reaction is proposed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
Reaction of 3,4,5,6,7,8-hexahydro-4-phenylquinazoline-2-thione with chloroacetic acid
Sharma, Rita,Kumar, Sudhir,Pujari, H K
, p. 425 - 426 (2007/10/02)
The title thione (I), prepared from 2-benzylidenecyclohexanone and thiourea, reacts with chloroacetic acid giving 6,7,8,9-tetrahydro-5H-5-phenylthiazoloquinazolin-3(2H)-one(II) which condenses with aromatic aldehydes to afford the arylidene derivat
