36422-60-3Relevant academic research and scientific papers
One-Pot Synthesis of 1,4-Dihydropyridine Derivatives and Their X-Ray Crystal Structures: Role of Fluorine in Weak Interactions
Begum, N. S.,Prasad, N. L.,Shashi, R.
, p. 938 - 947 (2020)
1,4-dihydropyridines, namely diethyl 4-(4-fluorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (1a), diethyl 2,6-dimethyl-4-(3,4,5-trimethoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate(1b), and diethyl 4-(3,4-dimethoxyphenyl)-2,6-dihydroxy-2
Pyridine C3-arylation of nicotinic acids accessible via a multicomponent reaction: an entry to all-substituted-3,4-diarylated pyridines
Guchhait, Sankar K.,Hura, Neha,Sinha, Kanchan,Panda, Dulal
, p. 8323 - 8331 (2017)
An efficient route for the synthesis of penta-substituted/functionalized-3,4-diarylated pyridines, biologically important templates, via pyridine C3-arylation of nicotinic acids has been developed. The poly-substituted nicotinic acid precursors were prepared by an established multicomponent condensation approach. This route shows an excellent opportunity for introducing versatile (hetero)aryls and other substituents/functionalities into the pyridine ring. Several of the synthesized compounds exhibited significant anti-proliferative properties.
Search for Antimicrobial Activity Among Fifty-Two Natural and Synthetic Compounds Identifies Anthraquinone and Polyacetylene Classes That Inhibit Mycobacterium tuberculosis
Pollo, Luiz A. E.,Martin, Erlon F.,Machado, Vanessa R.,Cantillon, Daire,Wildner, Leticia Muraro,Bazzo, Maria Luiza,Waddell, Simon J.,Biavatti, Maique W.,Sandjo, Louis P.
, (2021/02/12)
Drug-resistant tuberculosis threatens to undermine global control programs by limiting treatment options. New antimicrobial drugs are required, derived from new chemical classes. Natural products offer extensive chemical diversity and inspiration for synthetic chemistry. Here, we isolate, synthesize and test a library of 52 natural and synthetic compounds for activity against Mycobacterium tuberculosis. We identify seven compounds as antimycobacterial, including the natural products isobavachalcone and isoneorautenol, and a synthetic chromene. The plant-derived secondary metabolite damnacanthal was the most active compound with the lowest minimum inhibitory concentration of 13.07 μg/mL and a favorable selectivity index value. Three synthetic polyacetylene compounds demonstrated antimycobacterial activity, with the lowest MIC of 17.88 μg/mL. These results suggest new avenues for drug discovery, expanding antimicrobial compound chemistries to novel anthraquinone and polyacetylene scaffolds in the search for new drugs to treat drug-resistant bacterial diseases.
Synthesis and in vitro evaluation of Ca2 + channel blockers 1,4-dihydropyridines analogues against Trypanosoma cruzi and Leishmania amazonensis: SAR analysis
Pollo, Luiz A.E.,de Moraes, Milene H.,Cisilotto, Júlia,Creczynski-Pasa, Tania B.,Biavatti, Maique W.,Steindel, Mario,Sandjo, Louis P.
, p. 789 - 797 (2017/09/23)
Drugs containing the1,4-dihydropyridine (DHP) core have recently attracted attention concerning their antiparasitic effect against various species of Leishmania and Trypanosoma. This approach named drugs repositioning led to interesting results, which have prompted us to prepare 21 DHP's analogues. The 1,4-DHP scaffold was decorated with different function groups at tree points including the nitrogen atom (NH and N-phenyl), the aryl group attached to C-4 (various substituted aryl residues) and the carbon atoms 2 and 6 (bearing Ph or Me groups). Moreover, the products were evaluated for their cytotoxicity on three cancer and a non-tumoral cell lines. Only 6 of them were antiproliferative and their weak effect (CC50 comprised between 27 and 98 μM) suggested these DHPs as good candidates against the intracellular amastigote forms of L. amazonensis and T. cruzi. L. amazonensis was sensitive to DHPs 5, 11 and 15 (IC50 values at 15.11, 45.70 and 53.13 μM, respectively) while 12 of them displayed significant to moderate trypanocidal activities against T. cruzi. The best trypanocidal activities were obtained with compounds 2, 18 and 21 showing IC50 values at 4.95, 5.44, and 6.64 μM, respectively. A part of the N-phenylated DHPs showed a better selectivity than their NH analogues towards THP-1 cells. 4-Chlorophenyl, 4-nitrophenyl and 3-nitrophenyl residues attached to the carbon atom 4 turned to be important sub-structures for the antitrypanosomal activity.
Simple Br?nsted acid catalyzed C-H functionalization: Efficient access to poly-substituted pyridines
Lai, Shujun,Ren, Xuwen,Zhao, Jinzhong,Tang, Zhuo,Li, Guangxun
supporting information, p. 2957 - 2961 (2016/07/06)
An exceptionally simple and environmentally friendly methodology has been developed for directly functionalizing the benzylic C-H bond of the poly-substituted pyridines with aromatic imines. Simple Br?nsted acid catalysts including salicylic acid and TsOH were successfully employed. Different types of poly-substituted pyridines could be efficiently obtained with moderate yields. Traditional ways to such types of pyridines involved the aromatization of the corresponding Hantzsch 1,4-dihydropyridines, while this method greatly simplified the synthetic procedures.
Comparative study of catalytic potential of TBAB, BTEAC, and CTAB in one-pot synthesis of 1,4-dihydropyridines under aqueous medium
Ananda Kumar, T. Durai,Mohan,Subrahmanyam,Satyanarayana
, p. 574 - 582 (2014/01/23)
Convenient and straightforward tetrabutylammonium bromide (TBAB), benzyltrienthylammonium chloride (BTEAC), and cetyltrimethylammonium bromide (CTAB) catalyzed synthesis of 1,4-dihydropyridines (1,4-DHPs) in water was established for the first time. The catalytic potential of phase-transfer catalysts (PTCs) in three different concentrations was envisioned. Aryl aldehydes and hetero aryl aldehydes afforded good yields of 1,4-DHPs in TBAB and BTEAC reactions. In particular, furfuraldehyde and thienyl-2-carbaldehyde produced excellent yields. Isolation of the products through nonchromatographic methods, good to excellent yields, and benign reaction conditions are the major advantages of this protocol.
Silica sulfuric acid: An efficient heterogeneous catalyst for the one-pot synthesis of 1,4-dihydropyridines under mild and solvent-free conditions
Datta, Bandita,Pasha, M. Afzal
experimental part, p. 1180 - 1184 (2012/06/04)
A series of 1,4-dihydropyridines have been prepared by a one-pot condensation of aldehydes, ethyl acetoacetate, and ammonium acetate in the presence of a heterogeneous catalyst silica sulfuric acid at room temperature under solvent-free condition. This new protocol has the advantage of short reaction time and excellent yields, and is an environmentally benign route to the synthesis of 1,4-dihydropyridines.
Silica Sulfuric Acid: An Efficient Heterogeneous Catalyst for the One-Pot Synthesis of 1,4-Dihydropyridines under Mild and Solvent-Free Conditions
Datta, Bandita,Pasha, M. Afzal
, p. 1180 - 1184 (2016/04/10)
A series of 1,4-dihydropyridines have been prepared by a one-pot condensation of aldehydes, ethyl acetoacetate, and ammonium acetate in the presence of a heterogeneous catalyst silica sulfuric acid at room temperature under solvent-free condition. This new protocol has the advantage of short reaction time and excellent yields, and is an environmentally benign route to the synthesis of 1,4-dihydropyridines.
One-pot, solvent free synthesis of hantzsch 1, 4-dihydropyridines using β-cyclodextrin as a supramolecular catalyst
Patil, Dipak R.,Dalal, Dipak S.
experimental part, p. 477 - 483 (2012/04/23)
A novel, solvent free and efficient one pot synthesis of 1, 4-dihydropyridine derivatives was achieved in good yields via three component reaction of aldehydes, ethyl acetoacetate and ammonium acetate using inexpensive β- cyclodextrin as a supramolecular catalyst. The catalyst can be recovered and reused without loss of activity.
An efficient and solvent-free one-pot synthesis of 1,4-dihydropyridines under microwave irradiation
Kuraitheerthakumaran,Pazhamalai,Gopalakrishnan
experimental part, p. 1199 - 1202 (2012/01/06)
An efficient synthesis of 1,4-dihydropyridines using lanthanum oxide as a catalyst from aldehydes, β-ketoester and ammonium acetate without solvent under the irradiation of microwave is described. Compared with the classical Hantzsch reaction, this new me
