1657-28-9Relevant academic research and scientific papers
DERIVATIVES OF THE N-(PYRID-2-YL)AMIDES OF 3-AMINOCROTONIC ACID AS CHELATING LIGANDS
Dorokhov, V. A.,Baranin, S. V.,Dib, A.,Cherkasova, K. L.,Bochkareva, M. N.,Bogdanov, V. S.
, p. 765 - 769 (1992)
New chelating ligands, N-(pyrid-2-yl)amides of 4,4,4-trichloro-3-amino-2-cyanocrotonic acid have been synthesized from N-(pyrid-2-yl)amides of cyanoacetic acid and CCl3CN.It has been demostrated that by the action of butylthiodibutylborane they form binuclear boron chelate complexes.Analogous chelates have been obtained from the N-(pyrid-2-yl)amides of acetoacetic and 4,4,4-trichloro-3-aminocrotonic acids. Keywords: acylaminopyridines, trichloroacetonitrile, boron chelates
Pyrazole clubbed triazolo[1,5-a]pyrimidine hybrids as an anti-tubercular agents: Synthesis, in vitro screening and molecular docking study
Bhatt, Jaimin D.,Chudasama, Chaitanya J.,Patel, Kanuprasad D.
, p. 7711 - 7716 (2015)
A series of novel pyrazole linked triazolo-pyrimidine hybrids were synthesized and evaluated for their anti-tuberculosis activity against M.tb H37Rv strain. Some of the screened entities rendered promising anti-tb activity (MIC: 0.39 μg/mL) and were found non toxic against Vero cells (IC50: ≥20 μg/mL). Further, the docking study against wild type InhA enzyme of Mycobacterium tuberculosis using Glide reproduced the most active inhibitors (J21 and J27) with lowest binding energies and highest Glide XP scores demonstrating efficient binding to the active pocket. Additionally, the enzyme inhibition assay and ADME prediction of the active proved to be an attest to the possibility of developing compound J27 as a potent anti-tubercular lead.
Structure-Based Optimization of Small Molecule Human Galactokinase Inhibitors
Liu, Li,Tang, Manshu,Pragani, Rajan,Whitby, Frank G.,Zhang, Ya-Qin,Balakrishnan, Bijina,Fang, Yuhong,Karavadhi, Surendra,Tao, Dingyin,LeClair, Christopher A.,Hall, Matthew D.,Marugan, Juan J.,Boxer, Matthew,Shen, Min,Hill, Christopher P.,Lai, Kent,Patnaik, Samarjit
, p. 13551 - 13571 (2021/09/28)
Classic galactosemia is a rare disease caused by inherited deficiency of galactose-1 phosphate uridylyltransferase (GALT). Accumulation of galactose-1 phosphate (gal-1P) is thought to be the major cause of the chronic complications associated with this disease, which currently has no treatment. Inhibiting galactokinase (GALK1), the enzyme that generates galactose-1 phosphate, has been proposed as a novel strategy for treating classic galactosemia. Our previous work identified a highly selective unique dihydropyrimidine inhibitor against GALK1. With the determination of a co-crystal structure of this inhibitor with human GALK1, we initiated a structure-based structure-activity relationship (SAR) optimization campaign that yielded novel analogs with potent biochemical inhibition (IC50 100 nM). Lead compounds were also able to prevent gal-1P accumulation in patient-derived cells at low micromolar concentrations and have pharmacokinetic properties suitable for evaluation in rodent models of galactosemia.
Synthesis and anticonvulsant activity of some 1,4-dihydropyridine derivatives
Begum, Safia,Sirisha, Kalam
, p. 433 - 438 (2021/09/28)
A series of asymmetrical 4-alkyl/aryl-2,6-dimethyl-3-N-(aryl/heteroaryl)-carbamoyl-5-ethoxycarbonyl-1, 4-dihydropyridines 3a-d and symmetrical 4-alkyl/aryl-2,6-dimethyl-3,5-bis-(ethoxycarbonyl)-1,4-dihydropyridines 4a and 4b have been prepared by the condensation of various benzaldehydes, ethylacetoacetate, 2-aminopyridine or p-toludine in ethanol (Hantzch method). The structures of all the synthesized 1,4-dihydropyridine derivatives have been confirmed by spectral data (IR,1H NMR) and elemental analysis. Compounds 3a-c, 4a and 4b (10 mg/kg) have been evaluated for their anticonvulsant effect against pentylenetetrazole- induced convulsions with phenytoin (4 mg/kg) as the standard. The anticonvulsant potential of the newly synthesized compounds have been assessed on the basis of increase in latency (onset time) to induce convulsions; decrease in number of convulsions and increase in latency of death compared to control and standard.
HFIP-mediated strategy towards β-oxo amides and subsequent Friedel-Craft type cyclization to 2?quinolinones using recyclable catalyst
Kabi, Arup K.,Gujjarappa, Raghuram,Vodnala, Nagaraju,Kaldhi, Dhananjaya,Tyagi, Ujjawal,Mukherjee, Kalisadhan,Malakar, Chandi C.
supporting information, (2020/10/20)
A simple and cost-effective 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)-mediated protocol for the synthesis of β-oxo amides has been described by using amines and β-keto esters as substrates. The reaction conditions were found to be highly efficient towards the cleavage of C[sbnd]O bond and consequent formation of the products in excellent yields and selectivity. The obtained β-oxo amides were further transformed in to the synthetically useful 2?quinolinones via intramolecular Friedel-Craft type cyclization of aromatic ring using ferrites as a recyclable catalyst. A spectrum of substrates bearing broad range of functional groups were well tolerated under the reaction conditions. The proposed mechanistic pathways were substantially verified by literature and mass-spectroscopic evidences.
Metal and Solvent-Free Synthesis of 2H-Pyrido[1,2-a]pyrimidin-2-ones Catalyzed by Elemental Sulfur
Pavithra, Thangavel,Devi, E. Sankari,Nagarajan, Subbiah,Sridharan, Vellaisamy,Maheswari, C. Uma
supporting information, p. 6884 - 6887 (2019/11/11)
The efficiency of elemental sulfur for the synthesis of 2H-pyrido[1,2-a]pyrimidin-2-ones has been demonstrated. This strategy involves coupling of 2-aminopyridines and β-oxo esters under neat condition in the absence of external oxidant. The reaction does not require pre-functionalization of the substrates, thus making it an alternate approach for the synthesis of 2H-pyrido[1,2-a]pyrimidin-2-ones. The reaction was tolerant to several substituted 2-aminopyridines and β-oxo esters.
Targeting dormant tuberculosis bacilli: Results for molecules with a novel pyrimidone scaffold
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.
, p. 201 - 207 (2015/01/30)
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.
Facile eco-friendly synthesis of novel chromeno[4,3-b]pyridine-2,5-diones and evaluation of their antimicrobial and antioxidant properties
Jaggavarapu, Satyanarayana Reddy,Kamalakaran, Anand Solomon,Jalli, Ventkata Prasad,Gangisetty, Sravan Kumar,Ganesh, Munusswamy Ramanujam,Gaddamanugu, Gopikrishna
, p. 187 - 195 (2014/04/03)
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.
Facile eco-friendly synthesis of novel chromeno[4,3-b]pyridine-2,5-diones and evaluation of their antimicrobial and antioxidant properties
Jaggavarapu, Satyanarayana Reddy,Kamalakaran, Anand Solomon,Jalli, Ventkata Prasad,Gangisetty, Sravan Kumar,Ganesh, Munusswamy Ramanujam,Gaddamanugu, Gopikrishna
, p. 187 - 195 (2016/02/26)
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.]
Synthesis of some new 1,2,3,4-tetrahydropyrimidine-2-thione and their thiazolo[3,2-a]pyrimidine, thiazino and benzothiazepine derivatives
Fadda,Bondock,Khalil,Tawfik, Eman H.
, p. 838 - 843 (2013/08/23)
The starting N-(2-pyridyl)-6-methyl-4-phenyl-2-thioxo-1,2,3,4- tetrahydropyrimidine-5-carboxamide (4) was used as a key intermediate for the synthesis of new 1,2,3,4-tetrahydropyrimidine-2-thione and their thiazolo[3,2-a]pyrimidine, thiazino and benzothiazipen derivatives. The reaction of 4 with haloketones in ethanol catalyzed by base afforded the corresponding thiophenopyrimidine and pyrimidothiazipine derivatives 5-10. Methylation and formylation of 4 led to the pyrimidine derivatives 15 and 16, respectively. The preventative compounds were established on the basis of elemental and spectral data.
