KF/alumina catalyzed regioselective benzylation and benzoylation using solvent-free grind-stone chemistry

Jain, Shreyans K.; Meena, Samdarshi; Singh, Baljinder; Bharate, Jaideep B.; Joshi, Prashant; Singh, Varun Pratap; Vishwakarma, Ram A.; Bharate, Sandip B.

doi:10.1039/c2ra21154h

Cited by 10 publications

(6 citation statements)

References 48 publications

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“…Subsequent attempts discovered that the treatment of rohitukine with alkyl or benzyl halide in the presence of KF-alumina using grind-stone chemistry results in the regioselective formation of 7-Oethers. 52 Our motivation to synthesize this series (series A) was to check the tolerance of 7-hydroxyl group with respect to the biological activity. In series A compounds (e.g., 8a), the presence of a peak at δ 12.78 ppm in the 1 H NMR spectrum represents the presence of free phenolic OH at position C-5, which is H-bonded with C-4 carbonyl oxygen.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Discovery and Preclinical Development of IIIM-290, an Orally Active Potent Cyclin-Dependent Kinase Inhibitor

et al. 2018

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Rohitukine (1), a chromone alkaloid isolated from Indian medicinal plant Dysoxylum binectariferum, has inspired the discovery of flavopiridol and riviciclib, both of which are bioavailable only via intravenous route. With the objective to address the oral bioavailability issue of this scaffold, four series of rohitukine derivatives were prepared and screened for Cdk inhibition and cellular antiproliferative activity. The 2,6-dichloro-styryl derivative IIIM-290 (11d) showed strong inhibition of Cdk-9/T1 (IC 1.9 nM) kinase and Molt-4/MIAPaCa-2 cell growth (GI < 1.0 μM) and was found to be highly selective for cancer cells over normal fibroblast cells. It inhibited the cell growth of MIAPaCa-2 cells via caspase-dependent apoptosis. It achieved 71% oral bioavailability with in vivo efficacy in pancreatic, colon, and leukemia xenografts at 50 mg/kg, po. It did not have CYP/efflux-pump liability, was not mutagenic/genotoxic or cardiotoxic, and was metabolically stable. The preclinical data presented herein indicates the potential of 11d for advancement in clinical studies.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Discovery and Preclinical Development of IIIM-290, an Orally Active Potent Cyclin-Dependent Kinase Inhibitor

et al. 2018

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“…[54] Their work was based on an earlier observation where they have discovered oxidation of the methyl group of a chromone alkaloid via in situ generation of nitroso intermediate. [55] The authors described that the reaction was compatible with a variety of aldehydes and nitroarenes though steric factors influenced the outcome as ortho-substituted nitroarenes gave products in lower yields. Although it was suggested that thermal deoxyge-nation of nitroarene in the presence of MnO 2 transformed it into active nitroso intermediate, the precise mechanism of the reaction was not delineated.…”

Section: Amidation With Alcohols and Aldehydesmentioning

confidence: 99%

Direct Access to Amides from Nitro‐Compounds via Aminocarbonylation and Amidation Reactions: A Minireview

Barak

Batra

2021

The Chemical Record

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The ubiquity of the amide bond in functional molecules including proteins, natural products, pharmaceuticals, agrochemicals and materials provides impetus to design and develop newer strategies for the generation of this linkage. Owing to growing awareness about sustainability and development of benign strategies, the traditional route of synthesis of amides via reaction between carboxylic acids and amines in the presence of stoichiometric amount of coupling reagents is tagged to be harsh and wasteful. In one of the unconventional routes, nitro compounds are used directly as amine surrogates for preparing amides mostly via aminocarbonylation and amidation reactions. Typically, such processes involves nitroarenes owing to their propensity to transform into nitroso, hydroxylamine, diazo, hydrazine or aniline intermediates in situ under the influence of suitable catalyst or oxidant. This short review provides the comprehensive overview of these reactions including insight into the scope and their mechanisms.

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“…19,20 Previously, we isolated 19 rohitukine from the barks of D. binectariferum via chromatography on HP-20 resin by elution with increasing proportions of methanol in water. This protocol is time-consuming as it involves initial fractionation of the methanol extract (of bark) with silica-gel column chromatography followed by chromatography on HP-20 resin.…”

Section: Introductionmentioning

confidence: 99%

A chromatography-free isolation of rohitukine from leaves of Dysoxylum binectariferum: Evaluation for in vitro cytotoxicity, Cdk inhibition and physicochemical properties

Kumar

Guru

Jain

et al. 2016

Bioorganic & Medicinal Chemistry Letters

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KF/alumina catalyzed regioselective benzylation and benzoylation using solvent-free grind-stone chemistry

Cited by 10 publications

References 48 publications

Discovery and Preclinical Development of IIIM-290, an Orally Active Potent Cyclin-Dependent Kinase Inhibitor

Discovery and Preclinical Development of IIIM-290, an Orally Active Potent Cyclin-Dependent Kinase Inhibitor

Direct Access to Amides from Nitro‐Compounds via Aminocarbonylation and Amidation Reactions: A Minireview

A chromatography-free isolation of rohitukine from leaves of Dysoxylum binectariferum: Evaluation for in vitro cytotoxicity, Cdk inhibition and physicochemical properties

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