Synthesis and biological evaluation of novel Mannich bases of 2-arylimidazo[2,1-b]benzothiazoles as potential anti-cancer agents

Kumbhare, Ravindra M.; Katragunta, Kumar; Ramaiah, M. Janaki; Dadmal, Tulshiram L.; Pushpavalli, S. N. C. V. L.; Mukhopadhyay, Debasmita; Divya, Baddula; Devi, T. Anjana; Kosurkar, Umesh B.; Pal‐Bhadra, Manika

doi:10.1016/j.ejmech.2011.06.031

Cited by 69 publications

(16 citation statements)

References 34 publications

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“…A series of 3aminomethyl imidazo[2,1-b]benzothiazoles 99 ( Fig. 20) were evaluated for antiproliferative activity against hepatocellular carcinoma (HepG2), human breast (MCF-7) and human cervical (HeLa) cancer cell lines using MTT assay [127]. Mannich bases 99 inhibited the proliferation of cancer cells at concentrations lower than 10 mM, arrested the cell cycle at G2/M phase while downregulating cyclin B and upregulating Chk2 protein, and appeared to induce apoptosis based on the elevated levels of caspase-3.…”

Section: Anticancer and Cytotoxic Activitymentioning

confidence: 99%

Mannich bases in medicinal chemistry and drug design

Roman¹

2015

European Journal of Medicinal Chemistry

269

110

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The biological activity of Mannich bases, a structurally heterogeneous class of chemical compounds that are generated from various substrates through the introduction of an aminomethyl function by means of the Mannich reaction, is surveyed, with emphasis on the relationship between structure and biological activity. The review covers extensively the literature reports that have disclosed Mannich bases as anticancer and cytotoxic agents, or compounds with potential antibacterial and antifungal activity in the last decade. The most relevant studies on the activity of Mannich bases as antimycobacterial agents, antimalarials, or antiviral candidates have been included as well. The review contains also a thorough coverage of anticonvulsant, anti-inflammatory, analgesic and antioxidant activities of Mannich bases. In addition, several minor biological activities of Mannich bases, such as their ability to regulate blood pressure or inhibit platelet aggregation, their antiparasitic and anti-ulcer effects, as well as their use as agents for the treatment of mental disorders have been presented. The review gives in the end a brief overview of the potential of Mannich bases as inhibitors of various enzymes or ligands for several receptors.

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Section: Anticancer and Cytotoxic Activitymentioning

confidence: 99%

Mannich bases in medicinal chemistry and drug design

Roman¹

2015

European Journal of Medicinal Chemistry

269

110

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“…Both compounds have shown characteristic features of apoptosis. The compound 26f could be considered the potential lead for its development as a novel anticancer agent [ 53 ].…”

Section: Biological Activitiesmentioning

confidence: 99%

Mannich Bases: An Important Pharmacophore in Present Scenario

Bala

Sharma

Kajal

et al. 2014

International Journal of Medicinal Chemistry

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Mannich bases are the end products of Mannich reaction and are known as beta-amino ketone carrying compounds. Mannich reaction is a carbon-carbon bond forming nucleophilic addition reaction and is a key step in synthesis of a wide variety of natural products, pharmaceuticals, and so forth. Mannich reaction is important for the construction of nitrogen containing compounds. There is a number of aminoalkyl chain bearing Mannich bases like fluoxetine, atropine, ethacrynic acid, trihexyphenidyl, and so forth with high curative value. The literature studies enlighten the fact that Mannich bases are very reactive and recognized to possess potent diverse activities like anti-inflammatory, anticancer, antifilarial, antibacterial, antifungal, anticonvulsant, anthelmintic, antitubercular, analgesic, anti-HIV, antimalarial, antipsychotic, antiviral activities and so forth. The biological activity of Mannich bases is mainly attributed to α, β-unsaturated ketone which can be generated by deamination of hydrogen atom of the amine group.

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“…For several conversions employed in organic and pharmaceutical synthesis, especially, α-bromo carbonyl compounds have become a significant structural motif for the development of numerous biologically active compounds for instancethiazolidin-4-one, quinoxalines [10], cyclohexanone derivatives, thiophene, pyrazolo [1,5-α [11], thiadiazine and triazolo [3,4-b] [1,3,4]thiadiazine. Additionally, they are adaptable building blocks for the retro-synthesis of natural products.…”

Section: Synthesis Of Five-membered Heterocylces From Phenacyl Halidementioning

confidence: 99%

Phenacyl Bromide: An Organic Intermediate for Synthesis of Five- and Six-Membered Bioactive Heterocycles

Jangid¹,

Dhadda²

2020

Heterocycles - Synthesis and Biological Activities

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An environmentally friendly, economic synthetic protocol was advanced for synthesis of biologically and pharmacologically vital five-and six-membered heterocycles containing nitrogen, sulphur and oxygen as heteroatom. A series of thiazole derivatives was prepared by the reaction of substituted phenacyl halides and phenyl thiourea in the presence of TiO 2 nanoparticles (NPs) as nanocatalyst in DCM. Similarly, another series of six-membered heterocyclic compounds were synthesized by the reaction of phenacyl halides with phenylenediamine, 2-aminophenol, 2-aminobenzenethiol to produce corresponding products (1,4-quinoxaline, benzoxazine, benzothiazine) under catalytic effect of TiO 2 nanocatalyst. Analytical and spectral (FTIR, 1 H and 13 C NMR and SEM) techniques were employed for the structural elucidation of the synthesized compounds.

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Synthesis and biological evaluation of novel Mannich bases of 2-arylimidazo[2,1-b]benzothiazoles as potential anti-cancer agents

Cited by 69 publications

References 34 publications

Mannich bases in medicinal chemistry and drug design

Mannich bases in medicinal chemistry and drug design

Mannich Bases: An Important Pharmacophore in Present Scenario

Phenacyl Bromide: An Organic Intermediate for Synthesis of Five- and Six-Membered Bioactive Heterocycles

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