Green synthesis and anti-inflammatory studies of a series of 1,1-bis(heteroaryl)alkane derivatives (original) (raw)
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2012
Regioselective synthesis of some new dispiro[indane-2,3'-pyrrolidine-2',3"-indoline]-1,2",3triones (4a-j) has been generated by 1,3-dipolar cycloaddition reaction of 2-arylidene-indan-1,3diones (1a-j) as dipolarophiles with non-stabilized azomethine ylides, generated in situ via decarboxylative condensation of isatin (2) and sarcosine (3). Anti-inflammatory activity of the prepared compounds (4a-j) was determined in vivo by the acute carrageenan-induced paw edema in rats. Many of the prepared compounds exhibit considerable anti-inflammatory properties "at a dose of 10 mg/kg body weight", especially (4b) and (4c) which reveal promising activities relative to indomethacin which was used as a reference standard in this study.
Synthesis, antibacterial and anti-inflammatory activity of bis(indolyl)methanes
A series of bioactive bis(indolyl)methanes are synthesized by one-pot green reaction of indole with various substituted aldehydes by microwave irradiation under solvent free conditions. The antibacterial activity against Staphylococcus aureus and anti-inflammatory activity of the synthesized bis(indolyl)methanes are evaluated in vitro and compared to standard drugs tetracycline and diclofenac, respectively. The majority of the compounds showed good antibacterial and anti-inflammatory activity. Interestingly, compounds 3j, 3i, 3k and 3g exhibited much higher anti-inflammatory activity than the standard diclofenac drug and thus qualify for clinical trials to be used as an anti-inflammatory compound.
Molecules (Basel, Switzerland), 2018
PH46A is a single enantiomer and a member of the 1,2-indane dimer family. It has two contiguous stereogenic centers with , configurations, one of which being a quaternary center, which has been developed as a clinical candidate for the treatment of inflammatory and autoimmune conditions. The current synthetic route to PH46A involves the generation of an unwanted enantiomer (,)-, thus reducing the final yield significantly. Therefore, we have investigated potential alternatives to improve the efficiency of this synthesis. The first phase of the study has demonstrated proof of principle for a chiral alkylation of ketone using phase-transfer catalysis, providing a key intermediate ketone ()-. The parent alkaloids required for the synthesis of PH46A, quinine or cinchonidine, have also been identified. Promising enantiomeric excesses of up to 50% have been achieved to date, and the use of an alternative substrate, unsaturated ketone , has also opened up further avenues for optimisation i...
Central Asian Journal of Medical and Natural Science, 2023
This search included synthesized new hertocyclic derivatives from Isatin (T) via reaction with 4-aminobenzoic acid to give (T2) ,and with SOCl2 to give compound (T1) , esterfication to give (T3), reacted with hydrazine to give (T4) compound ,and with anhydrides to give(T5,T6) .The schiff base (T10) prepared from benzylaldehyde and (T9) perpared fram (T2) and thiocarbohydrazide .(T8) compound synthesized fram (T2) and semicarbzide by aring closer reaction in NaOH. This (T1-T10) compounds were measured biological and anticancer activity and give high good activity with (IC50=42.18,45.02 for compounds 12 and 3).
Arabian Journal of Chemistry, 2000
Aminoacetylenic isoindoline-1,3-dione derivatives were synthesized from the reaction of potassium phthalimide with propargyl bromide to generate 2-(prop-2-yn-1-yl)isoindoline-1,3-dione (ZM1). Treatment of 2-(prop-2-yn-1-yl)isoindoline-1,3-dione with appropriate cyclic amines through Mannich reaction yielded five desired aminoacetylenic isoindoline-1,3-diones called, ZM2–ZM6. The IR, NMR and elemental analysis were consistent with the assigned structures. These synthetic compounds, except ZM6, produced significant (p<0.05–0.01) dose-related inhibition of carrageenan-induced edema
Synthesis of some novel fused oxo- and thiopyrimidinesviaan intramolecular friedel-crafts reaction
Journal of Heterocyclic Chemistry, 2007
1H-Indeno[1,2-d]pyrimidine-2,5(3H,9bH)-dione derivatives 2(a-i) and 2,3-dihydro-2-thioxo-1Hindeno[1,2-d]pyrimidine-5(9bH)-ones 2(j-q) were synthesized via an intramolecular Friedel-Crafts reaction between the aryl and ester group of ethyl 6-methyl-4-aryl-2-oxo-1,2,3,4-tetrahydropyrimidine-5carboxylates 1a-i, and their thioxo analogs using AlCl 3 and acetyl chloride in nitrobenzene. Yields of the products, after washing with THF, were of the order of 45-69%. IR and NMR spectroscopy together with elemental analysis were used for identification of these compounds.
Research on Chemical Intermediates, 2016
4-Sulfophthalic acid (4-H 3 SPA) solution 50 wt% in H 2 O has been effectively catalyzed the synthesis of a series of biologically relevant bis(indolyl)methanes by the electrophilic substitution of indole derivatives on aldehyde compounds and 4,4 0-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s by condensing 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one with various aldehydes under aqua conditions at room temperature. 3,3 0-(Arylmethylene)-bis-4-hydroxycoumarins have also been synthesized in the presence of 0.1 mL (0.262 mmol) of 4-H 3 SPA solution 50 wt% in H 2 O at 80°C. The procedure is simple and the expected bis-heterocyclic compounds were isolated in good to excellent yields. The present protocol provides the benefits of convenience, mild reaction conditions, eco-friendliness, and no use of hazardous organic solvents. Keywords Bis(indolyl)methanes Á Bispyrazoles Á Biscoumarins Á 4-Hydroxycoumarin Á Indole derivatives Á 5-Methyl-2-phenyl-2,4-dihydro-3Hpyrazol-3-one Á 4-Sulfophthalic acid