- Phenothiazine and amide-ornamented novel nitrogen heterocyclic hybrids: synthesis, biological and molecular docking studies
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The synthesis of novel hybrids, namely, phenothiazine and amide-ornamented nitrogen heterocycles (25-34) has been accomplished utilizing a multi-step synthetic protocol and the structures have been established based on physical and spectral techniques. Of these, the hybrids possessing meta-nitro (26), para-fluoro (28), meta- and para-methyl (31), ortho-bromo (33) and ortho- and para-dimethyl (34) phenyl carboxamide scaffolds exhibited superior anti-inflammatory profiles over the standard diclofenac sodium. A hybrid integrated with a para-fluorophenyl carboxamide moiety (28) showed the highest DPPH radical scavenging activity among the chemical entities synthesized. Furthermore, the results of anticancer evaluations implied that the hybrid tethered with a phenyl carboxamide structural unit (29) exerted superior activity when compared with other hybrids against the pancreatic cancer cells SW1990 and AsPC1. Molecular docking between the hybrid 29 and B-cell lymphoma 2 reflects its appreciable binding affinity (-8.84 kcal mol-1). The results revealed that these chemical entities can serve as potent biological agents and/or efficient intermediates for the construction of potent biological agents.
- Iniyaval, Shunmugam,Karuppasamy, Ayyanar,Lim, Wei-Meng,Mai, Chun-Wai,Padmavathy, Krishnaraj,Ramalingan, Chennan,Sivaramakarthikeyan, Ramar
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p. 4049 - 4060
(2020/03/19)
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- Phenothiazine and amide-ornamented dihydropyridines: Via a molecular hybridization approach: Design, synthesis, biological evaluation and molecular docking studies
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A series of novel phenothiazinyldihydropyridine dicarboxamides 7a-7j was synthesized by adopting a multi-step synthetic strategy and characterized through physical and spectral techniques. Among them, the chemical entities with para-fluoro (7d), ortho-bromo and-fluoro (7f and 7i), ortho- A nd para-methyl (7e) and meta- A nd para-methoxy (7h) substituents exhibited either similar or superior anti-inflammatory activities with respect to the standard drug diclofenac sodium. Besides, the chemical entities with ortho-bromo and-fluoro substituents as well as meta-nitro substituents (7f, 7g and 7i) showed enhanced radical scavenging activities when compared to standard ascorbic acid. Furthermore, anticancer studies revealed that the meta- A nd para-chloro-substituted molecule 7a exerted the best activity against all the pancreatic cancer cells tested. Also, appreciable binding affinity (-8.10 kcal mol-1) was observed during molecular docking between B-cell lymphoma 2 and 7a. The structural diversifications of the potent chemical entities besides further exploration in connection with the biological profiles of the same are underway.
- Sivaramakarthikeyan, Ramar,Iniyaval, Shunmugam,Padmavathy, Krishnaraj,Liew, Hui-Shan,Looi, Chin-King,Mai, Chun-Wai,Ramalingan, Chennan
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p. 17046 - 17057
(2019/11/14)
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- Acetyl aceotphenone amine preparation method of the compound
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The invention provides a preparation method of an acetoacetanilide compound. The method comprises the steps of performing diacetylation reaction on aniline compounds and diketene in an organic solvent under anaerobic conditions to obtain the acetoacetanilide compound. The acetoacetanilide compound is prepared under the anaerobic conditions; the acetoacetanilide compound prepared by using the method has a relatively high melting point, thereby being beneficial for applications of the acetoacetanilide compound. In addition, the acetoacetanilide compound prepared by using the method provided by the invention is not easy to agglomerate, and the preparation method of the acetoacetanilide compound, provided by the invention, is relatively low in energy consumption. Experimental results show that the melting point of the acetoacetanilide compound prepared by using the method provided by the invention is 82.5-103 DEG C.
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Paragraph 0035; 0036; 0038
(2017/02/24)
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- An efficient synthesis, characterization, and antimicrobial screening of tetrahydropyrimidine derivatives
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Several new substituted 1,2,3,4-tetrahydropyrimidine derivatives 2a-h have been synthesized by the modified Biginelli and Hantzsch reactions and compounds were characterized by spectral techniques. All compounds were evaluated for their in vitro antimicrobial activity against different strains of Gram-negative (E. coli and P. aeruginosa) and Gram-positive (S. aureus and S. pyogenus) bacteria and selected fungi C. albicans, A. niger, and A. clavatus using serial Broth dilution method (Mueller-Hinton broth dilution method). Compound 2e was found active against both Gram-negative and -positive bacterial strains used for present study, while compound 2b was good active against Gram-negative and S. pyogenus bacterial strains. Compounds 2a-h were not that much significant against (C. albicans, A. niger, and A. clavatus) selected fungal strains. Springer Science+Business Media 2013.
- Godhani, Dinesh R.,Dobariya, Purvesh B.,Jogel, Anand A.,Sanghani, Anil M.,Mehta, Jignasu P.
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p. 2417 - 2425
(2014/05/06)
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- Synthesis of Pyridin-2(1H)-one derivatives: Temperature-dependent selectivity
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Two alternative methods for the synthesis of biologically important pyridin-2(1H)-one derivatives have been developed. The behavior of enamine 1 with aromatic amines in an aqueous solution of HCl resulted in the formation of substituted enamines 2a-f at ambient temperature. The obtained product enamines 2a-f, upon treatment with 2,2,6-trimethyl-4H-1,3-dioxin-4-one, generated pyridin-2(1H)-one derivatives 5a-f along with the unwanted side products 8a-f. However, the exclusive formation of pyridin-2(1H)-one derivatives 5a-f was achieved when starting from β-enaminones 3a-f, which were synthesized successfully from enamine 1 and aromatic amines at elevated temperatures. Compounds 2 and 3 have been used as precursors in the synthesis of pyridin-2(1H)-one derivatives. Temperature-dependent reaction diversity was observed for enamine 1 and the exclusive formation of pyridin-2(1H)-one derivatives 5 was possible.
- Chikhalikar, Sandip,Bhawe, Vijay,Jachak, Madhukar,Ghagare, Maruti
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experimental part
p. 6085 - 6091
(2011/12/02)
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- Synthesis, screening for antitubercular activity and 3D-QSAR studies of substituted N-phenyl-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxamides
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Multi-drug resistance to commonly used antitubercular drugs has propelled the development of new structural classes of antitubercular agents. This paper reports the synthesis, evaluation and 3D-QSAR analysis of a set of substituted N-phenyl-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamides as antitubercular agents. Substituted acetoacetanilides were reacted with various aromatic aldehydes and urea which yielded the tetrahydropyrimidine derivatives with a phenyl carbamoyl group at C5 position, and with various substitutions on the 4-phenyl and the N-phenyl aromatic rings. All compounds were screened for antitubercular activity against Mycobacterium tuberculosis H37Rv strain. The QSAR models were generated on a training set of 23 molecules. The molecules were aligned using the atom-fit and field-fit techniques. The CoMFA and CoMSIA models generated on the molecules aligned by the atom-fit method show a correlation coefficient (r2) of 0.98 and 0.95 with cross-validated r2(q2) of 0.68 and 0.58, respectively. The 3D-QSAR models were externally validated against a test set of 7 molecules for which the predictive r2 (rpred2) is recorded as 0.41 and 0.32 for the CoMFA and CoMSIA models, respectively. The CoMFA and CoMSIA contours helped to design some new molecules with improved activity.
- Virsodia, Vijay,Pissurlenkar, Raghuvir R.S.,Manvar, Dinesh,Dholakia, Chintan,Adlakha, Priti,Shah, Anamik,Coutinho, Evans C.
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p. 2103 - 2115
(2008/12/23)
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- Unexpected formation of new bicyclic γ-lactams by dimerization of α-chloroacetoacetanilides
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Novel and unusual dimerization reaction of α-chloroacetoacetanilide under basic reaction condition to give structurally unique 6-oxa-3-azabicyclo[3.1.0]hexane was described.
- Han, Minsoo,Nam, Kee-Dal,Hahn, Hoh-Gyu,Shin, Dongyun
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p. 5217 - 5219
(2008/12/20)
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- Process for the Preparation of N-Arylamides of Acetoacetic Acid
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Continuous procedure to the manufacture of acetoacetic acid arylamide comprises reaction of diketen with primary/secondary aromatic amine in the presence of water and followed by reactive distillation.
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Page/Page column 4-5
(2008/06/13)
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- Acetoacetarylamides
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Novel acetoacetarylamides in the form of a solidified melt which are in a form which can be used in industry and is easy to handle and which has a water content of from 3 to 15 percent by weight. These novel acetoacetarylamides have been used for the preparation of colored pigments or agrochemical active ingredients.
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