Design and optimization of quinazoline derivatives as melanin concentrating hormone receptor 1 (MCHR1) antagonists

Sasmal, Sanjita; Balaji, Gade; Reddy, Hariprasada Reddy Kanna; Balasubrahmanyam, D.; Gadipelli, Srinivas; Kyasa, ShivaKumar; Sasmal, Pradip K.; Khanna, Ish; Talwar, Rashmi; Joghee, Suresh; Jadhav, Vikram P.; Syed, Mustafa; Shashikumar, Dhanya; Reddy, K. Harinder; Sebastián, Víctor; Frimurer, Thomas M.; Rist, Øystein; Elster, Lisbeth; Högberg, Thomas

doi:10.1016/j.bmcl.2012.03.050

Cited by 50 publications

(39 citation statements)

References 32 publications

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“…Tetrahydrofuran was distilled from sodium benzophenone ketyl and degassed thoroughly with dry argon directly before use. Unless otherwise noted, organic extracts were dried with anhydrous Na2SO4, filtered through a fitted glass funnel and concentrated with a rotary evaporator (20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30). Flash chromatography was performed with silica gel (200-300 mesh) by using the mobile phase indicated.…”

Section: Methodsmentioning

confidence: 99%

“…Researchers have already determined many therapeutic activities of quinazoline derivatives, including anticancer [3][4][5][6], antiinflammation [7,8], antibacterial [9][10][11][12], antivirus [13], anticytotoxin [14], antispasm [15], antituberculosis [16], antioxident [17], antimalarial [18], antihypertension [19], antiobesity [20], antipsychotic [21] and antidiabetes [22], etc.…”

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confidence: 99%

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Design, Synthesis and Molecular Properties Prediction of Novel Quinazoline Derivatives as Potent Antibacterial Agents

Eswararao¹,

Venkataramireddy²,

Srinivasareddy³

et al. 2017

Asian J. Chem.

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Design, Synthesis and Molecular Properties Prediction of Novel Quinazoline Derivatives as Potent Antibacterial Agents

Eswararao¹,

Venkataramireddy²,

Srinivasareddy³

et al. 2017

Asian J. Chem.

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“…Among these GW 856464 [211], AMG076 [212] and NGD-4715 [213] achieved phase 1 clinical investigations. Trials to optimize quinazolines [214][215][216][217][218][219], as (40) (Figure 9(a)), revealed GW 803430 (GW3430; [214]), ATC0175 and ATC0065 [215] which were shown efficacious in rodent depression models [197]. However, ATC0175 and ATC0065 are binding with high affinity not only to MCH1-R but also to subtypes of the 5 HT receptor [197] suggesting that the antidepressiv effect of the MCH1-R antagonist is not due to MCH1-R alone.…”

Section: Non-peptide Ligands Of Mch-receptorsmentioning

confidence: 99%

Non-peptide ligands in the characterization of peptide receptors at the interface between neuroendocrine and mental diseases

Pissarek¹,

Disko²

2013

WJNS

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Hypothalamic receptors for neuropeptide Y, melaninconcentrating hormone, melanocortins and orexins/ hypocretins as well as for the downstream signaling corticotrophic factor have been discussed broadly for their influence on food intake and reward but also on several psychiatric disorders. For the development of non-peptide ligands for the in vivo detection of alterations in density and affinity of such G-protein coupled (GPCRs) peptide receptors the requirements to affinity and pharmacokinetics have been shifted to thresholds markedly distict from classical GPCRs to dissociation constants < 0.5 nM, partition coefficients log P < 3.5 and transcellular transport ratios, e.g. for the permeability glycoprotein transporter, below 3. Nevertheless, a multitude of compounds has been reported originally as potential therapeutics in the treatment of obesity among which some are suitable candidates for labeling as PET or SPECT-tracers providing receptor affinities even below 0.1 nM. These could be unique tools not only for better understanding of the mechanism of obesity but also for investigations of extrahypothalamic role of "feeding receptors" at the interface between neuroendocrine and mental diseases.

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“…Quinazoline derivatives, which belong to the N-containing heterocyclic compounds, have caused universal concerns due to their biopharmaceutical activities. Researchers have already determined many therapeutic activities of quinazoline derivatives, including anticancer [1][2][3][4] , antiinflammatory 5,6 , antibacterial [7][8][9][10] , analgesic 5,9 , antiviral 11 , anticytotoxic 12 , antispasm 9,13 , antituberculosis 14 , antioxidant 15 , antimalarial 16 , antihypertension 17 , antiobesity 18 , antipsychotic 19 , anti-diabetics 20 , etc. Medicinal chemists synthesized quinazoline derivatives with different biological activities by installing various active groups to the quinazoline moiety.…”

Section: Introductionmentioning

confidence: 99%

Utility of 4-Aryl-8-arylidene-3, 4, 5, 6, 7, 8-hexa-hydroquinazoline-2-thiol for the Synthesis of Some New Heterocycles as Antioxidant Agents

2017

Chem Sci Trans

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Abstract:The present study deals with the synthesis and reactions of 4-aryl-8-arylidene-3,4,5,6,7,8-hexahydroquinazoline-2-thiol (1). Hydrazinolysis of compound 1 yielded hexahydroquinazolinyl hydrazine 2. Acetylation of compound 2 yielded [1,2,4] triazolo [3,4-b] quinazoline derivative 3. The reaction of compound 2 with diethyl oxalate and ethyl acetoacetate afforded hexahydro quinazolin-2-yl-hydrazinyl-2-oxoacetate 9 and hexahydroquinazolin-2-yl-3-oxobutane hydrazide 10. Treatment of compound 1 with chloroacetyl chloride gave tetrahydro-2H-thiazolo [2,3-b] quinazolin-3(5H)-one 13 which was used as a key for the synthesis of a series of heterocyclic compounds (14-19). The structures of the newly synthesized compounds were elucidated on the basis of elemental analysis, spectral data. The antioxidant activities of some new synthesized compounds have been screened. Compounds 2, 3, 12, 13, 15, 16 and 19 showed antioxidant activity using the DPPH method.

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Design and optimization of quinazoline derivatives as melanin concentrating hormone receptor 1 (MCHR1) antagonists

Cited by 50 publications

References 32 publications

Design, Synthesis and Molecular Properties Prediction of Novel Quinazoline Derivatives as Potent Antibacterial Agents

Design, Synthesis and Molecular Properties Prediction of Novel Quinazoline Derivatives as Potent Antibacterial Agents

Non-peptide ligands in the characterization of peptide receptors at the interface between neuroendocrine and mental diseases

Utility of 4-Aryl-8-arylidene-3, 4, 5, 6, 7, 8-hexa-hydroquinazoline-2-thiol for the Synthesis of Some New Heterocycles as Antioxidant Agents

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