Isoxazole-based derivatives from Baylis–Hillman chemistry: assessment of preliminary hypolipidemic activity

Patra, Arundhati; Batra, Sanjay; Bhaduri, A. P.; Khanna, Ashok; Chander, Ramesh; Dikshit, Madhu

doi:10.1016/s0968-0896(03)00105-6

Cited by 30 publications

(20 citation statements)

References 39 publications

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“…PHL activity is expressed as lmole FFA released/h/L (Nityanand and Kapoor, 1986), may be due to reactivation of lipolytic enzymes (the PHLA) for early clearance of lipids from circulation in triton-induced hyperlipidemia. We have successfully used this model for the evaluation of the lipid-lowering activity of natural products and synthetic drugs (Khanna et al, 1994;Patra et al, 2003). The present investigation with cholesterol-rich HFD-fed hyperlipidemic animals showed that A. indicus fruit extract could stimulate PHLA and hepatic LPL activity, both of which play a key role in lipid catabolism and their utilization in body (Brown and Goldstein, 1986).…”

Section: Discussionmentioning

confidence: 74%

Hypolipidemic activity of Anthocephalus indicus (kadam) in hyperlipidemic rats

et al. 2008

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The hypolipidemic action of Anthocephalus indicus (family, Rubiaceae: Hindi name, Kadam) fruit extract has been studied in hyperlipidemic rats fed a triton-and cholesterol-rich high-fat diet. In triton WR-1339-induced hyperlipidemic rats, feeding with the fruit extract (500 mg/kg b.w.) exerted a lipid-lowering effect as assessed by reversal of plasma levels of total cholesterol, phospholipids, and triglyceride following reactivation of the post-heparin lipolytic activity. In another model, chronic feeding of this natural product (500 mg/kg, b.w.) to animals simultaneously fed a high-fat diet for 30 days caused lowering of lipid levels in plasma and liver accompanied with stimulation of hepatic lipolytic activity. The hypolipidemic activity of Anthocephalus indicus fruit extract iscompared with guggulipid, a known lipid-lowering drug, in both models.

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Section: Discussionmentioning

confidence: 74%

Hypolipidemic activity of Anthocephalus indicus (kadam) in hyperlipidemic rats

et al. 2008

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“…Consequently 9 was subjected to reaction with NaBH 4 in S N 2Ј-and S N 2-fashion to afford compounds 10 and 11, respectively following reported procedure (Scheme 2). [7] Compound 10 was obtained as a mixture of E and Z isomers. Without separating these isomers, 10 was subjected to reduction in the presence of Fe/AcOH.…”

Section: Resultsmentioning

confidence: 99%

Expeditious Synthesis of Imidazole‐ and Pyrrole‐Fused Benzodiazocines

Mishra

Batra

2010

Eur J Org Chem

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A straightforward strategy for the synthesis of imidazolefused benzodiazocine from 1-(2-nitrophenyl)-1H-imidazole-2-carbaldehyde via Morita-Baylis-Hillman reaction followed by reductive intramolecular cyclization is described. Alternatively the Horner-Wadsworth-Emmons reaction of this substrate with triethyl phosphonoacetate yielded (E)-ethyl 3-(1-(2-nitrophenyl)-1H-imidazol-2-yl)acrylate which upon sequential reduction, saponification and amide coupling fur-

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“…In principle, a product similar to compound 9 could be generated from compound 12 or 13, which in turn can be easily synthesized through reaction of sodium borohydride with the acetate (7) under appropriate conditions. 9,10 In order to obtain chemical evidence for the formation of compounds 9-10, compounds 12b and 13b were subjected to hydrogenation in the presence of RaneyNi. As envisaged both reactants led to the product 9b in good yield.…”

Section: Resultsmentioning

confidence: 99%

“…[1][2][3][4][5] This ability of the isoxazole-ring besides making it a useful synthetic intermediate also evokes interest to understand reasons for biological activity because our interest in the Baylis-Hillman chemistry of isoxazolecarbaldehydes has not only led us to generate novel isoxazole-based synthetic intermediates but has also led to identification of bioactive compounds. [6][7][8][9][10] The hydrogenation studies of the Baylis-Hillman adduct and their corresponding derivatives under heterogeneous catalytic conditions with Pd-C and rhodium have been earlier reported. [11][12][13][14] While these detailed studies address the issue of diastereoselectivity in the reduced product under different additives and solvent conditions, the fate of the Baylis-Hillman adducts during hydrogenation in the presence of Raney-Ni remains unreported.…”

Section: Introductionmentioning

confidence: 99%