19134-89-5Relevant academic research and scientific papers
Unexpected solvent/substitution-dependent inversion of the enantioselectivity in Michael addition reaction using chiral phase transfer catalysts
Kottala Vijaya, Ponmuthu,Murugesan, Sepperumal,Siva, Ayyanar
, p. 5209 - 5212 (2015)
New cinchonium salts bearing 5,5′-bis(methyl)-2,2′-bipyridine 1 group show solvent/substitution-dependent reversal of enantioselectivity. When used as chiral phase transfer catalyst in the asymmetric Michael addition of chalcones with diethylmalonate within two hours these catalysts result in high chemical yield (up to 98%) and enantiomeric excess (up to 99%) under lower concentrations of base and cold conditions.
Efficient base-free asymmetric one-pot synthesis of spiro[indoline-3,3′-pyrrolizin]-2-one derivatives catalyzed by chiral organocatalyst
Chithiraikumar, Chinnadurai,Ponmuthu, Kottala Vijaya,Harikrishnan, Muniyasamy,Malini, Nelson,Sepperumal, Murugesan,Siva, Ayyanar
, p. 895 - 909 (2020/10/29)
A 1,3-dipolar cycloaddition reaction has been performed under organocatalytic conditions with high enantioselectivity by the utilization of bipyridine-based chiral quaternary ammonium bromide as an organocatalyst. Here, the reaction of 1,3-dipolar cycloaddition of azomethine ylide generated in situ from the decarboxylative condensation of α-amino acids and non-enolizable 1,2-diketones to the above dipolarophiles takes place.
Lewis acid catalyst system for Claisen-Schmidt reaction under solvent free condition
Halpani, Chandni G.,Mishra, Satyendra
, (2020/07/16)
Ca(OTf)2 in combination with NBu4.BF4 was established to function as an efficient catalyst system for one-pot Claisen-Schmidt condensation under neat conditions. Substituted acetophenones and benzaldehydes were coupled in situ to afford their corresponding chalcones in excellent yields. The method, with a broad range of substrate tolerance and mild operational conditions can produce assorted chalcone derivatives in moderate to high yields from easily accessible starting materials.
Microwave-irradiated synthesis and biological evaluation of 3,5-diaryl-1-phenyl-2-pyrazolines as antibacterial and anti-inflammatory agents
Kumar, Anjan,Rout, Sradhasini,Panda, Jnyanaranjan,Sahoo, Biswa Mohan,Banik, Bimal Krishna
, p. 1321 - 1326 (2020/06/27)
In a wide search program towards a biologically active antibacterial and anti-inflammatory agents, a series of 3,5-diaryl-1-phenyl-2-pyrazoline have been synthesized with excellent yields employing microwave techniques starting from substituted α,β-unsaturated carbonyl compounds which undergo cyclization reactions with phenylhydrazine. The structures of newly synthesized compounds were characterized and confirmed on the basis of FT-IR, 1H NMR and mass spectral analyses. The synthesized compounds 3,5-diaryl-1-phenyl-2-pyrazolines had shown significant activity against Staphylococcus aureus (MTCC 87), Escherichia coli (MTCC 40), Pseudomonas aeruginosa (MTCC 424) and Proteus vulgaris (MTCC 426) by cup plate method using tetracycline-SD 037 as a reference standard. The anti-inflammatory property of 1,3,5-diaryl-1-phenyl-2-pyrazolines were screened by using carragenan induced paw edema method in Wistar rat. The anti-inflammatory activities were comparable to that of the standard drug diclofenac. The safety of 3,5-diaryl-1-phenyl-2-pyrazolines were reflected by toxicity studies.
Synthesis, anti-inflammatory, analgesic, COX-1/2 inhibition activities and molecular docking study of pyrazoline derivatives
Abdel-Sayed, Maged A.,Bayomi, Said M.,El-Sherbeny, Magda A.,Abdel-Aziz, Naglaa I.,Eltahir, Kamal Eldin H.,Shehatou, George S.G.,Abdel-Aziz, Alaa A.-M.
, p. 2032 - 2042 (2016/04/20)
Design, synthesis and pharmacological activities of a group of 1,3,5-trisubstituted pyrazolines were reported. The chemical structures of the synthesized compounds have been assigned on the basis of IR, MS, 1H NMR, and 13C NMR spectral analyses. The synthesized 1,3,5-trisubstituted pyrazoline derivatives were evaluated in vivo for anti-inflammatory, analgesic activities and in vitro for COX-1/2 inhibition assay. Among the tested compounds, derivatives 4h, 6e, 7a, 7e, and 9 showed more potent anti-inflammatory and analgesic activities than the reference drug celecoxib. On the basis of their higher activities in the in vivo studies compared with celecoxib, the five compounds 4h, 6e, 7a, 7e and 9 were selected to test their inhibitory activities against ovine COX-1/2 using an in vitro cyclooxygenase inhibition assay. Docking study of compounds 7a, 7e and 9 into the COX-2 binding site revealed a similar binding mode to SC-558, a selective COX-2 inhibitor.
Antimycobacterial and anti-inflammatory activities of substituted chalcones focusing on an anti-tuberculosis dual treatment approach
Ventura, Thatiana Lopes Biá,Calixto, Sanderson Dias,De Azevedo Abrahim-Vieira, Bárbara,De Souza, Alessandra Mendon?a Teles,Mello, Marcos Vinícius Palmeira,Rodrigues, Carlos Rangel,De Mariz E Miranda, Leandro Soter,De Souza, Rodrigo Octavio Mendon?a Alves,Leal, Ivana Correa Ramos,Lasunskaia, Elena B.,Muzitano, Michelle Fraz?o
, p. 8072 - 8093 (2015/05/20)
Tuberculosis (TB) remains a serious public health problem aggravated by the emergence of M. tuberculosis (Mtb) strains resistant to multiple drugs (MDR). Delay in TB treatment, common in the MDR-TB cases, can lead to deleterious life-threatening inflammation in susceptible hyper-reactive individuals, encouraging the discovery of new anti-Mtb drugs and the use of adjunctive therapy based on anti-inflammatory interventions. In this study, a series of forty synthetic chalcones was evaluated in vitro for their anti-inflammatory and antimycobacterial properties and in silico for pharmacokinetic parameters. Seven compounds strongly inhibited NO and PGE2 production by LPS-stimulated macrophages through the specific inhibition of iNOS and COX-2 expression, respectively, with compounds 4 and 5 standing out in this respect. Four of the seven most active compounds were able to inhibit production of TNF-α and IL-1β. Chalcones that were not toxic to cultured macrophages were tested for antimycobacterial activity. Eight compounds were able to inhibit growth of the M. bovis BCG and Mtb H37Rv strains in bacterial cultures and in infected macrophages. Four of them, including compounds 4 and 5, were active against a hypervirulent clinical Mtb isolate as well. In silico analysis of ADMET properties showed that the evaluated chalcones displayed satisfactory pharmacokinetic parameters. In conclusion, the obtained data demonstrate that at least two of the studied chalcones, compounds 4 and 5, are promising antimycobacterial and anti-inflammatory agents, especially focusing on an anti-tuberculosis dual treatment approach.
A new class of bifunctional chiral phase transfer catalysts for highly enantioselective asymmetric epoxidation of α,β-unsaturated ketones at ambient temperature
Ashokkumar, Veeramanoharan,Balasaravanan, Rajendiran,Sadhasivam, Velu,Jenofar, Seenisultanmaideen Mehtob,Siva, Ayyanar
, p. 127 - 136 (2015/09/15)
A new type of bis-quaternary ammonium bromide as chiral multifunctional phase transfer catalysts derived from readily available inexpensive cinchona alkaloids has been developed and evaluated for the enantioselective asymmetric epoxidation of various chalcones in the presence of lower concentrations of various oxidants, bases, solvents and ambient temperature conditions. Under optimized reaction conditions, highest chemical yields of up to 98% along with the excellent enantioselectivities of about 99% were obtained by using the cinchona based chiral multifunctional phase transfer catalysts.
Synthesis of some 3,5-diaryl-2-isoxazoline derivatives in ionic liquids media
Safaei-Ghomi, Javad,Ghasemzadeh, Mohammad Ali
experimental part, p. 733 - 739 (2012/09/22)
Biologically active isoxazoline derivatives were efficiently synthesized in excellent yields and in smaller reaction times using mild, effective and environmentally friendly butylmethylimidazolium bromide as the solvent and catalyst. By use of this cataly
Rasta Resin-PPh3-NBniPr2 and its use in one-pot wittig reaction cascades
Teng, Yan,Lu, Jinni,Toy, Patrick H.
experimental part, p. 351 - 359 (2012/04/18)
A new triarylphosphine-tertiary amine bifunctional polymeric reagent has been prepared and used effectively in a variety of one-pot Wittig reactions. The design of this reagent resolved a deficiency of a previously reported related material, and allowed it to perform more efficiently in such reactions. Furthermore, it was readily recyclable, and was also successfully applied in cascade processes involving one-pot Wittig reactions followed by either a conjugate reduction or a reductive aldol reaction. In these reaction cascades, the phosphine oxide groups generated in the Wittig reaction served as the catalyst for the subsequent reaction. All in one pot! A recyclable, second-generation heterogeneous bifunctional polymer bearing phosphine and amine groups has been synthesized and showed enhanced utility in one-pot Wittig reactions compared to a previously reported related material. This polymer was also used in Wittig reaction cascade processes in which the oxidized polymer formed in the one-pot Wittig reaction served as the catalyst in a subsequent conjugate reduction or reductive aldol reaction (see scheme).
Synthesis, molecular docking and evaluation of thiazolyl-pyrazoline derivatives as EGFR TK inhibitors and potential anticancer agents
Lv, Peng-Cheng,Li, Dong-Dong,Li, Qing-Shan,Lu, Xiang,Xiao, Zhu-Ping,Zhu, Hai-Liang
scheme or table, p. 5374 - 5377 (2011/10/12)
Fourty-two thiazolyl-pyrazoline derivatives were synthesized to screen for their EGFR kinase inhibitory activity. Compound 4-(4-chlorophenyl)-2-(3-(3,4- dimethylphenyl)-5-p-tolyl-4,5-dihydro-1H-pyrazol-1-yl)thiazole (11) displayed the most potent EGFR TK inhibitory activity with IC50 of 0.06 μM, which was comparable to the positive control. Molecular docking results indicated that compound 11 was nicely bound to the EGFR kinase. Compound 11 also showed significant antiproliferative activity against MCF-7 with IC 50 of 0.07 μM, which would be a potential anticancer agent.
