The Morita–Baylis–Hillman adducts of β-aryl nitroethylenes with other activated alkenes: synthesis and anticancer activity studies

Dadwal, Mamta; Mohan, Renu; Panda, Dulal; Mobin, Shaikh M.; Namboothiri, Irishi N. N.

doi:10.1039/b512267h

Cited by 74 publications

(38 citation statements)

References 21 publications

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“…In the above scenario, our endeavors to achieve reactions between nitroalkenes and various electrophiles such as formaldehyde, [10][11] activated carbonyl compounds [12] / imines [13] /alkenes, [14] and azodicarboxylates [15] in the presence of imidazole or DMAP as the catalyst have met with success in recent years. The anti-cancer activities exhibited by many MBH adducts of nitroalkenes at low micromolar concentrations, through targeting of tubulins/microtubules, [11,13,14] and the potential application of MBH adducts as valuable intermediates in the synthesis of amino alcohols, amino acids, and heterocycles encouraged us to expand the scope of the MBH reaction by introducing aliphatic nitroalkenes and aromatic nitrodienes as substrates for the first time.…”

Section: Introductionmentioning

confidence: 98%

“…The anti-cancer activities exhibited by many MBH adducts of nitroalkenes at low micromolar concentrations, through targeting of tubulins/microtubules, [11,13,14] and the potential application of MBH adducts as valuable intermediates in the synthesis of amino alcohols, amino acids, and heterocycles encouraged us to expand the scope of the MBH reaction by introducing aliphatic nitroalkenes and aromatic nitrodienes as substrates for the first time. This report is the full version of our preliminary communication relating to the reactions between aromatic nitroalkenes and various activated non-enolizable carbonyl compounds.…”

Section: Introductionmentioning

confidence: 99%

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Morita–Baylis–Hillman Reactions Between Conjugated Nitroalkenes or Nitrodienes and Carbonyl Compounds

Deb¹,

Shanbhag²,

Mobin³

et al. 2009

Eur J Org Chem

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Morita-Baylis-Hillman (MBH) reactions between conjugated nitroalkenes or nitrodienes and various carbonyl compounds such as glyoxylate, trifluoropyruvate, pyruvaldehyde, oxomalonate, ninhydrin, and formaldehyde have been extensively investigated. The reactions proceeded smoothly in the presence of DMAP (40-100 mol-%) in acetonitrile and in some cases also in that of imidazole (100 mol-%) in CHCl 3 or THF, to provide the multifunctional adducts in good to excellent yields. The reactions catalyzed by DMAP in acetonitrile were superior to the imidazole-catalyzed reactions both in terms of the rate of reaction and in terms of the isolated yields of the MBH adducts. The catalytic roles played by DMAP and imidazole in these reactions, vis-à-vis other MBH cata-

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Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Morita–Baylis–Hillman Reactions Between Conjugated Nitroalkenes or Nitrodienes and Carbonyl Compounds

Deb¹,

Shanbhag²,

Mobin³

et al. 2009

Eur J Org Chem

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“…A wide range of functional groups can be introduced in MBH adducts by the selection of three relevant constituents namely, activated alkene, electrophile and catalyst . MBH adducts such as α‐hydroxymethylated and α‐aminoalkylated conjugated nitroalkenes has been found to inhibit human cervical cancer cells . Moreover, derivatives of MBH adducts have also exhibited hypolipidemic, antifungal, antitumoral and several other activities in the biological sphere .…”

Section: Introductionmentioning

confidence: 99%

Application of a Nanosensor Based on MWCNT‐Sodium Dodecyl Sulphate Modified Electrode for the Analysis of a Novel Drug, Alpha‐Hydrazinonitroalkene in Human Blood Serum

et al. 2017

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The sensitivity enhancing properties of sodium dodecyl sulphate (SDS) and multi‐walled carbon nanotubes (MWCNTs) were associated to construct a nanosensor based on carbon paste electrode (CPE) by adopting drop cast method. The drop cast method makes use of minimum modifier and the entire modified surface of the sensor is available for the analyte. Surface characterization of the electrodes was carried out using FE‐SEM and EDX. EIS was used for the electrochemical characterization. We report for the first time the electrochemical analysis based on the oxidation of the ‐OH group of a novel drug, alpha‐hydrazinonitroalkene (I) which was found to have antibacterial and antimicrobial properties. The electron transfer kinetic parameters such as the charge transfer coefficient α and heterogeneous rate constant k′ were calculated and they have been found to be 0.64 and 9.62 × 10−2 cm s−1 respectively. The linear response ranges for (I) obtained at this sensor are 1.0 × 10−7 M − 7.0 × 10−7 M and 1.0 × 10−6 M – 4.5 × 10−5 M with a detection limit of (7.03 ± 0.41) × 10−8 M (S/N=3). The interference study suggested that the sensor was free from 1000‐fold excess of UA in the determination of (I). It was important to note that the sensor completely eliminated Ascorbic acid (AA) signal which offered a significant analytical advantage for the determination of the drug at this sensor. The practical usefulness of the modified sensor was demonstrated by the analysis of (I) in blood serum.

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“…For these reasons, to our best knowledge, no enantioselective intermolecular crossed-conjugate addition has been reported. [8] To study this transformation, our group investigated the double Michael addition of nitroalkenes and enones. With a b-alkyl group on the nitroalkene, the crossed-conjugate addition was successfully achieved through an irreversible b-hydride elimination (Scheme 2 A).…”

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confidence: 99%

Enantioselective Intermolecular Crossed‐Conjugate Additions between Nitroalkenes and α,β‐Enals through a Dual Activation Strategy

Zhong¹,

Chen²,

Petersen³

et al. 2009

Angew Chem Int Ed

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The Morita–Baylis–Hillman adducts of β-aryl nitroethylenes with other activated alkenes: synthesis and anticancer activity studies

Abstract: The Morita-Baylis-Hillman (MBH) adducts of beta-aryl nitroethylenes with methyl vinyl ketone (MVK) and acrylate, formed in moderate to good yield when mediated by imidazole/LiCl in THF at room temperature, inhibit HeLa cell proliferation by binding to tubulin.

Cited by 74 publications

References 21 publications

Morita–Baylis–Hillman Reactions Between Conjugated Nitroalkenes or Nitrodienes and Carbonyl Compounds

Morita–Baylis–Hillman Reactions Between Conjugated Nitroalkenes or Nitrodienes and Carbonyl Compounds

Application of a Nanosensor Based on MWCNT‐Sodium Dodecyl Sulphate Modified Electrode for the Analysis of a Novel Drug, Alpha‐Hydrazinonitroalkene in Human Blood Serum

Enantioselective Intermolecular Crossed‐Conjugate Additions between Nitroalkenes and α,β‐Enals through a Dual Activation Strategy

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