- Synthesis and in vitro Antidiabetic Screening of Novel Dihydropyrimidine Derivatives
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Abstract: A series of N-substituted-6-methyl-4-{4-[5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl]methoxyphenyl}-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides have been synthesized by the condensation of newly synthesized {4-[5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl]methoxy}benzaldehyde with variously substituted acetoacetanilides and urea in the presence of ethanol. The synthesized compounds have been characterized by 1H, 13C NMR, IR spectroscopy, and mass spectrometry. All synthesized compounds were evaluated for in vitro antidiabetic activity using the α-amylase inhibition assay with the 3,5-dinitrosalicylic acid (DNSA) reagent.
- Lalpara,Vachhani,Hadiyal,Goswami,Dubal
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p. 241 - 246
(2021/04/02)
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- 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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- Effective microwave synthesis of bioactive thieno[2,3-d]pyrimidines
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A series of novel 2-Amino-3-cyanothiophenes (2a-2j) were synthesized using heterogeneous base (K2CO3) supported Gewald reaction. Cyclization of 2a-j with formamide and urea in conventional heating as well as microwave irradiation gave thieno[2,3-d]pyrimidines (3a-3j) and thieno[2,3-d]pyrimidin-2(1H)-ones(4a-4j) respectively. The reaction rates were faster and yields were higher in the microwave conditions. The structures of the compounds were confirmed with elemental analysis, mass spectral analysis, FTIR, 1H NMR and 13C NMR techniques. All the synthesized compounds were subjected to antimicrobial activity (MIC) in vitro by broth dilution method and exhibited a moderate antimicrobial activity.
- Khatri, Taslimahemad T.,Shah, Viresh H.
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p. 3354 - 3358
(2017/05/22)
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- Design, Multicomponent Synthesis and Characterization of Diversely Substituted Pyrazolo[1,5-a] Pyrimidine Derivatives
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The synthesis of various heterocyclic compounds using acetoacetanilide[AAA], we have demonstrated that acetoactanilide are versatile intermediate for the synthesis of pyrazolopyrimidine derivatives. Thus, to explore further, we sought that the reaction of various acetoactanilide, an appropriate aldehyde and 5-amino-N-cyclohexyl-3-(methylthio)-1H-pyrazole-4-carboxamide in the presence of base in isopropyl alcohol could be an effective strategy to furnish the novel pyrazolopyrimidine derivatives. Here we describe the novel synthetic methodology for the fused pyrazolopyrimidines.
- Ghelani, Satish M.,Naliapara, Yogesh T.
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p. 1843 - 1851
(2016/11/23)
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- COMPOUND HAVING AZO SKELETON, PIGMENT DISPERSANT, PIGMENT COMPOSITION, PIGMENT DISPERSION, AND TONER
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A compound that improves the dispersibility of pigments in non-water-soluble solvents is provided. A pigment dispersant, a pigment composition, a pigment dispersion, and a toner in which this compound is used are also provided. This compound has a polymer
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Paragraph 0314
(2016/08/17)
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- COMPOUND HAVING AZO SKELETON STRUCTURE, PIGMENT-DISPERSING AGENT, PIGMENT COMPOSITION, PIGMENT DISPERSION, AND TONER
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The present invention provides a compound capable of improving the dispersibility of color pigments in a water-insoluble solvent; and a pigment-dispersing agent. The present invention also provides a pigment composition, a pigment dispersion, and a toner,
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Paragraph 0334; 0336
(2016/10/17)
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- Discovery and Optimization of Novel, Selective Histone Methyltransferase SET7 Inhibitors by Pharmacophore- and Docking-Based Virtual Screening
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Histone methyltransferases are involved in various biological functions, and these methylation regulating enzymes' abnormal expression or activity has been noted in several human cancers. Within this context, SET domain-containing (lysine methyltransferase) 7 (SET7, also called KMT7, SETD7, SET9) is of increasing significance due to its diverse roles in biological functions and diseases, such as diabetes, cancers, alopecia areata, atherosclerotic vascular disease, HIV, and HCV. In this study, DC-S100, which was discovered by pharmacophore- and docking-based virtual screening, was identified as the hit compound of SET7 inhibitor. Structure-activity relationship (SAR) analysis was performed on analogs of DC-S100 and according to the putative binding mode of DC-S100, structure modifications were made to improve its activity. Of note, compounds DC-S238 and DC-S239, with IC50 values of 4.88 and 4.59 μM, respectively, displayed selectivity for DNMT1, DOT1L, EZH2, NSD1, SETD8, and G9a. Taken together, DC-S238 and DC-S239 can serve as leads for further investigation as SET7 inhibitors and the chemical toolkits for functional biology studies of SET7.
- Meng, Fanwang,Cheng, Sufang,Ding, Hong,Liu, Shien,Liu, Yan,Zhu, Kongkai,Chen, Shijie,Lu, Junyan,Xie, Yiqian,Li, Linjuan,Liu, Rongfeng,Shi, Zhe,Zhou, Yu,Liu, Yu-Chih,Zheng, Mingyue,Jiang, Hualiang,Lu, Wencong,Liu, Hong,Luo, Cheng
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p. 8166 - 8181
(2015/11/09)
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- Targeting dormant tuberculosis bacilli: Results for molecules with a novel pyrimidone scaffold
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Our inability to completely control TB has been due in part to the presence of dormant mycobacteria. This also renders drug regimens ineffective and is the prime cause of the appearance of drug-resistant strains. In continuation of our efforts to develop novel antitubercular agents that especially target dormant mycobacteria, a set of 55 new compounds belonging to the pyrimidone class were designed on the basis of CoMFA and CoMSIA studies, and these were synthesized and subsequently tested against both the dormant and virulent BCG strain of M. tuberculosis. Some novel compounds have been identified which selectively inhibit the dormant tuberculosis bacilli with significantly low IC50 values. This study reports the second molecule after TMC-207, having the ability to inhibit tuberculosis bacilli exclusively in its dormant phase. The synthesis was accomplished by a modified multicomponent Biginelli reaction. A classification model was generated using the binary QSAR approach - recursive partitioning (RP) to identify structural characteristics related to the activity. Physicochemical, structural, topological, connectivity indices, and E-state key descriptors were used for generation of the decision tree. The decision tree could provide insights into structure-activity relationships that will guide the design of more potent inhibitors. This paper reports the second molecule after TMC-207, with the ability to inhibit tuberculosis bacilli in its dormant phase. The paper reports molecules with a novel Pyrimidone Scaffold, the synthesis of which was accomplished with a modified multi-component Biginelli reaction. A classification model was generated using recursive partitioning (RP) technique to identify structural characteristics of the molecules with their varying activities.
- Joshi, Rohit R.,Barchha, Avinash,Khedkar, Vijay M.,Pissurlenkar, Raghuvir R. S.,Sarkar, Sampa,Sarkar, Dhiman,Joshi, Rohini R.,Joshi, Ramesh A.,Shah, Anamik K.,Coutinho, Evans C.
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p. 201 - 207
(2015/01/30)
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- METHOD FOR PRODUCING COMPOUND HAVING COLORANT STRUCTURE AT MAIN CHAIN TERMINAL OF POLYMER, AND PIGMENT DISPERSANT, PIGMENT COMPOSITION, PIGMENT DISPERSION AND TONER CONTAINING COMPOUND OBTAINED BY THE PRODUCTION METHOD
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To provide a method for producing a compound that enhances dispersibility of a pigment of respective colors in a water-insoluble solvent, as well as a pigment dispersant, and a pigment composition, a pigment dispersion and a toner having a good tinting po
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Paragraph 0236
(2015/11/16)
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- METHOD OF PRODUCING A COMPOUND HAVING A COLORANT STRUCTURE, AND TONER CONTAINING A COMPOUND OBTAINED BY THE PRODUCTION METHOD
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Provided are a method of producing a compound having a colorant structure suitable for a pigment dispersant, and a pigment dispersant, a pigment composition, a pigment dispersion, and a toner each containing the compound. The production method is a method
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Paragraph 0216
(2015/11/18)
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- COMPOUND HAVING AZO SKELETON STRUCTURE, PIGMENT DISPERSING AGENT, PIGMENT COMPOSITION, PIGMENT DISPERSION, AND TONER
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PROBLEM TO BE SOLVED: To provide a compound that improves dispersibility of color pigments in a non-water-soluble solvent and a pigment dispersing agent, and also provide a pigment composition, a pigment dispersion, and a toner which have satisfactory tin
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Paragraph 0300; 0301
(2016/11/09)
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- Facile eco-friendly synthesis of novel chromeno[4,3-b]pyridine-2,5-diones and evaluation of their antimicrobial and antioxidant properties
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Rapid and facileaccess to novel chromeno[4,3-b]pyridine-2,5-dione derivatives was achieved by a mild base catalysed reaction of 4-chloro-3-formylcoumarin and acetoacetamides in PEG-300 as recyclable solvent. The compounds were evaluated for their antimicrobial activities against 3 Gram-positive and 3 Gram-negative bacteria (Staphylococcus epidermis, Vibrio parahaemolyticus, Bacillus subtilis, Escherichia coli, Staphylococcus aureus and Klebsiella pneumonia) with Cefotaxime control. They were further subjected to antioxidant studies using DPPH test with ascorbic acid control. While compounds 5d and 5k showed promising broad spectrum antibacterial properties against all the evaluated bacteria, compound 5g exhibited good antioxidant properties. Indian Academy of Sciences.
- Jaggavarapu, Satyanarayana Reddy,Kamalakaran, Anand Solomon,Jalli, Ventkata Prasad,Gangisetty, Sravan Kumar,Ganesh, Munusswamy Ramanujam,Gaddamanugu, Gopikrishna
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p. 187 - 195
(2014/04/03)
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- Facile eco-friendly synthesis of novel chromeno[4,3-b]pyridine-2,5-diones and evaluation of their antimicrobial and antioxidant properties
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Rapid and facile access to novel chromeno[4,3-b]pyridine-2,5-dione derivatives was achieved by a mild base catalysed reaction of 4-chloro-3-formylcoumarin and acetoacetamides in PEG-300 as recyclable solvent. The compounds were evaluated for their antimicrobial activities against 3 Gram-positive and 3 Gram-negative bacteria (Staphylococcus epidermis, Vibrio parahaemolyticus, Bacillus subtilis, Escherichia coli, Staphylococcus aureus and Klebsiella pneumonia) with Cefotaxime control. They were further subjected to antioxidant studies using DPPH test with ascorbic acid control. While compounds 5d and 5k showed promising broad spectrum antibacterial properties against all the evaluated bacteria, compound 5g exhibited good antioxidant properties. [Figure not available: see fulltext.]
- Jaggavarapu, Satyanarayana Reddy,Kamalakaran, Anand Solomon,Jalli, Ventkata Prasad,Gangisetty, Sravan Kumar,Ganesh, Munusswamy Ramanujam,Gaddamanugu, Gopikrishna
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p. 187 - 195
(2016/02/26)
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- COMPOUND HAVING AZO SKELETON STRUCTURE, PIGMENT-DISPERSING AGENT, PIGMENT COMPOSITION, PIGMENT DISPERSION, AND TONER
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The present invention provides a compound capable of improving the dispersibility of yellow, magenta, cyan, and black pigments in a water-insoluble solvent and a pigment-dispersing agent. The present invention also provides a pigment composition, a pigment dispersion, and a toner, which have satisfactory tinting strength. The present invention relates to a compound having a structure in which an azo skeleton structure is bound to a polymer portion via a linking group in the azo skeleton structure.
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Paragraph 0298
(2014/11/13)
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- Synthesis and pharmacological screening of some 1,4-dihydropyridine and their derivatives for anticonvulsant activity
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A new series of 1,4-dihydropyridine and their derivatives have been synthesized and the structures of the compounds have been confirmed by IR and NMR. The title compounds are evaluated for anticonvulsant activity by maximal electroshock method. Some of these compounds have been found to exhibit excellent anticonvulsant activity.
- Pattan, Shashikant R.,Purohit,Rasai,Mallya,Marihal,Khade,Paschapur
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p. 626 - 629
(2008/09/20)
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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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- Synthesis and characterization of N-acylaniline derivatives as potential chemical hybridizing agents (CHAs) for wheat (Triticum aestivum L.)
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Induction of male sterility by deployment of chemical hybridizing agents (CHAs) are important in heterosis breeding of self-pollinated crops like wheat, wherein the male and female organs are in the same flower. Taking a lead from the earlier work on rice, a total of 25 N-acylanilines comprising of malonanilates, acetoacetanilides, and acetanilides (including halogenated acetanilides) were synthesized and screened as CHAs on three genotypes of wheat, viz., PBW 343, HD 2046, and HD 2733 at 1500 ppm in the winter of 2001-2002. The N-acylanilines containing variations at the acyl and aromatic domain were synthesized by condensation of substituted anilines with appropriate diesters, acid chlorides, or monoesters. The test compounds with highly electronegative groups such as F/Br at the para position of the aryl ring were identified as the most potent CHAs, causing higher induction of male sterility. A variation of N-substitution at the side chain generally furnished analogues like 4′-fluoroacetoacetanilide (7) and ethyl 4′-fluoromalonanilate (1), which induced 89.12 and 84.66% male sterility, respectively, in PBW 343. Among halogenated acetanilides, the increasing number of chlorine atoms in the side chain led to an increase in the activity of 4′-fluoro (23) and 4′-bromo (24) derivatives of trichoroacetanilides, which induced >87% male sterility. Quantitative structure-activity relationship (QSAR) models indicated the positive contributions of the field effect exemplified by the Swain-Lupton constant (Fp) and negative contributions of the Swain-Lupton resonance constant (R) for the aromatic substitution. The positive influences of parachor (P) for the acyl domain have been underlined. These leads will be significant in explaining the CHA fit in the macromolecular receptor site. The CHAs appeared to act by causing an imbalance in the acid-base equilibrium in pollen mother cells resulting in dissolution of the callose wall by premature callase secretion.
- Chakraborty, Kajal,Devakumar
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p. 6800 - 6808
(2007/10/03)
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- MECHANISM OF ACETOACETYLATION OF SUBSTITUED ANILINES
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Kinetics have been studied of the reaction of diketene with substituted anilines, and the reaction rate has been found to depend on relative permitivity of the system.The rate and equilibrium constants have been calculated by combination of rate and equilibrium relations with the relation by Amis; the constants correlate with the Hammett substituent constants.The reaction does not proceed as a simple bimolecular process.A reaction mechanism has been suggested.
- Knizek, Jiri,Lejdar, Erhard,Vetesnik, Pavel
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p. 365 - 374
(2007/10/02)
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- Cyclocondensations of Acetoacetanilides with 1,3,5-Trinitrobenzene-Substituent Effect in the Formation of Bicyclononane Derivatives
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Kinetics of cyclicondensation reaction of acetoacetanilide and substituted acetoacetanilides with 1,3,5-trinitrobenzene in the presence of triethylamine have been studied in 75percentDMSO-water(v/v) at 30, 35 and 40 deg C.Electron donating groups accelerate the rate of the reaction.Strongly electron withdrawing groups in the para-position require the use of ?--values for a better correlation of the rate constants.The reaction constants and the resonance parameters have been calculated.Isokinetic relationship has been established.Equilibrium constants for the formationof sodium salts of bicyclononane derivatives from sodium salts of acetoacetanilides and TNB have been calculated.
- Gnanadoss, Lalitha,Radha, N.
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p. 1077 - 1081
(2007/10/02)
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