Synthesis and antimosquito properties of 2,6-substituted benzo[d]thiazole and 2,4-substituted benzo[d]thiazole analogues against Anopheles arabiensis

Venugopala, Katharigatta N.; Manjula, K.; Nayak, Susanta K.; Subrahmanya, Bhat K.; Vaderapura, Jayashankaragowda P.; Chalannavar, Raju K.; Gleiser, Raquel M.; Odhav, Bharti

doi:10.1016/j.ejmech.2013.04.061

Cited by 61 publications

(30 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…47 Benzamide derivative 22 was successfully obtained in 70% yield by refluxing a mixture of benzamide, benzaldehyde, and 8-hydroxyquinoline in dichloroethane in the presence of catalytic p -toluenesulfonic acid. 48 Synthesis of imine analog 23 required heating a mixture of ammonium carbamate, benzaldehyde (2 equivalents), and 8-hydroxyquinoline in ethanol at 125 °C for 12-15 hours.…”

Section: Resultsmentioning

confidence: 99%

8-Hydroxyquinoline-based inhibitors of the Rce1 protease disrupt Ras membrane localization in human cells

Mohammed

Hampton

Ashall

et al. 2016

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

Ras converting enzyme 1 (Rce1) is an endoprotease that catalyzes processing of the C-terminus of Ras protein by removing -aaX from the CaaX motif. The activity of Rce1 is crucial for proper localization of Ras to the plasma membrane where it functions. Ras is responsible for transmitting signals related to cell proliferation, cell cycle progression, and apoptosis. The disregulation of these pathways due to constitutively active oncogenic Ras can ultimately lead to cancer. Ras, its effectors and regulators, and the enzymes that are involved in its maturation process are all targets for anticancer therapeutics. Key enzymes required for Ras maturation and localization are the farnesyltransferase (FTase), Rce1, and isoprenylcysteine carboxyl methyltransferase (ICMT). Among these proteins, the physiological role of Rce1 in regulating Ras and other CaaX proteins has not been as fully explored. Small-molecule inhibitors of Rce1 could be useful as chemical biology tools to understand further the downstream impact of Rce1 on Ras function and serve as potential leads for cancer therapeutics. Structure-activity relationship (SAR) analysis of a previously reported Rce1 inhibitor, NSC1011, has been performed to generate a new library of Rce1 inhibitors. The new inhibitors caused a reduction in Rce1 in vitro activity, exhibited low cell toxicity, and induced mislocalization of EGFP-Ras from the plasma membrane in human colon carcinoma cells giving rise to a phenotype similar to that observed with siRNA knockdowns of Rce1 expression. Several of the new inhibitors were more effective at mislocalizing K-Ras compared to a potent farnesyltransferase inhibitor (FTI), which is significant because of the preponderance of K-Ras mutations in cancer.

show abstract

Section: Resultsmentioning

confidence: 99%

8-Hydroxyquinoline-based inhibitors of the Rce1 protease disrupt Ras membrane localization in human cells

Mohammed

Hampton

Ashall

et al. 2016

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

show abstract

“…In this communication and in continuation of our work on the development of pharmacologically active heterocyclic compounds6,34,35 and screening of heterocyclic compounds for properties of polymorphism,36–38 we have synthesized 1,2,3-triazole hybrid with DHPMs using aryl azide as well as DHPMs having a terminal alkynyl group, which was synthesized by the four component Biginelli-like cyclocondensation reaction ( tert -butyl β-ketoester, propargyl alcohol, aryl aldehyde, and urea) along with catalytic amount of Cu(OAc) 2 and sodium ascorbate in a 1:2 ratio of acetone and water as a solvent at room temperature as shown in Figure 1.…”

Section: Introductionmentioning

confidence: 84%

Design, synthesis, and characterization of (1-(4-aryl)-1<em>H</em>-1,2,3-triazol-4-yl)methyl, substituted phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates against <em>Mycobacterium tuberculosis</em>

Venugopala¹,

Rao²,

Bhandary³

et al. 2016

DDDT

View full text Add to dashboard Cite

The novel (1-(4-aryl)-1H-1,2,3-triazol-4-yl)methyl, substituted phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate derivatives were synthesized by the click reaction of the dihydropyrimidinones, bearing a terminal alkynyl group, with various substituted aryl azides at room temperature using a catalytic amount of Cu(OAc)2 and sodium ascorbate in a 1:2 ratio of acetone and water as a solvent. The newly synthesized compounds were characterized by a number of spectroscopic techniques, such as infrared, liquid chromatography-mass spectrometry, 1H, and 13C nuclear magnetic resonance along with single crystal X-ray diffraction. The current procedure for the synthesis of 1,2,3-triazole hybrids with dihydropyrimidinones is appropriate for the synthesis of a library of analogs 7a-l and the method accessible here is operationally simple and has excellent yields. The title compounds 7a-l were evaluated for their in vitro antitubercular activity against H37RV and multidrug-resistant strains of Mycobacterium tuberculosis by resazurin microplate assay plate method and it was found that compound 7d was promising against H37RV and multidrug-resistant strains of M. tuberculosis at 10 and 15 μg/mL, respectively.

show abstract

“…Dihydropyridine derivatives have shown larvicidal activity against the medically important mosquito species Aedes aegypti and Culex quinquefasciatus (Diptera) . In view of such promising pharmacological activities of 1,4‐DHPs and in continuation of our efforts to develop novel anti‐malarial agents we herein undertake the synthesis of a series of new‐fangled bis(4‐substituted benzyl) 4‐(4‐substituted phenyl)‐2,6‐dimethyl‐1,4‐dihydropyridine‐3,5‐dicarboxylate derivatives 5a–h as depicted in Scheme . Furthermore, it is also of interest to screen such heterocyclic compounds for the existence of polymorphs and their implications in the observed biological property.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of a novel series of 1,4‐dihydropyridine analogues for larvicidal activity against Anopheles arabiensis

et al. 2017

Self Cite

View full text Add to dashboard Cite

The new-fangled bis(4-substituted benzyl) 4-(4-substitued phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate derivatives were synthesized by the union of substituted aryl aldehyde, tert-butyl acetoacetate, ammonium carbonate with 4-substituted benzyl alcohol via Hantzsch ester synthesis in aqueous medium under catalyst-free conditions. The newly synthesized compounds were characterized by spectroscopic techniques such as IR, NMR ( H and C), ESI mass, elemental analysis, and single-crystal X-ray diffraction. The characterized title compounds were evaluated for the larvicidal activity against Anopheles arabiensis by standard WHO larvicidal assay method using Temephos as standard at 4 μg/ml. The title compounds bis(4-methoxybenzyl) 2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate and bis(4-chlorobenzyl) 2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate exhibited promising larvicidal activity at 65.6% and 72.2%, respectively, when compared with the standard compound at 98.9%.

show abstract

Synthesis and antimosquito properties of 2,6-substituted benzo[d]thiazole and 2,4-substituted benzo[d]thiazole analogues against Anopheles arabiensis

Cited by 61 publications

References 45 publications

8-Hydroxyquinoline-based inhibitors of the Rce1 protease disrupt Ras membrane localization in human cells

8-Hydroxyquinoline-based inhibitors of the Rce1 protease disrupt Ras membrane localization in human cells

Design, synthesis, and characterization of (1-(4-aryl)-1<em>H</em>-1,2,3-triazol-4-yl)methyl, substituted phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates against <em>Mycobacterium tuberculosis</em>

Synthesis and characterization of a novel series of 1,4‐dihydropyridine analogues for larvicidal activity against Anopheles arabiensis

Contact Info

Product

Resources

About