Synthesis of Some New Halogenated N-Thiazolyl Substituted Hydroxy Acid Amides and Their Use as Possible Fungicides

Tripathy, H.; Pradhan, D. G.; Dash, B. C.; Mahapatra, G. N.

doi:10.1080/00021369.1973.10860856

Cited by 15 publications

(10 citation statements)

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“…All the compounds were recrystallized from ethanol; their HPLC purity exceeded 97%. By microwave-assisted synthesis reaction times were shortened from hours [34,35,36,37] to minutes, and yields of most compounds (except 2-NO 2 derivative 8a ) were more than 65%, for details see Section 3.2.…”

Section: Resultsmentioning

confidence: 99%

Antibacterial and Herbicidal Activity of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides

et al. 2013

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Abstract:In this study, a series of twenty-two ring-substituted 3-hydroxy-Nphenylnaphthalene-2-carboxanilides were prepared and characterized. The compounds were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four Staphylococcus strains and against two mycobacterial species. 3-Hydroxy-N-(2-methoxyphenyl)naphthalene-2-carboxamide showed OPEN ACCESSMolecules 2013, 18 7978 high biological activity (MIC = 55.0 µmol/L) against S. aureus as well as methicillinresistant strains. N-(2-Fluorophenyl)-3-hydroxynaphthalene-2-carboxamide showed higher activity (MIC = 28.4 µmol/L) against M. marinum than the standard isoniazid and 3-hydroxy-N-(4-nitrophenyl)naphthalene-2-carboxamide expressed higher activity (MIC = 13.0 µmol/L) against M. kansasii than the standard isoniazid. Cytotoxicity assay of effective antimicrobial compounds was performed using the human monocytic leukemia THP-1 cell line. The PET-inhibiting activity expressed by IC 50 value of the most active compound 3-hydroxy-N-(3-nitrophenyl)naphthalene-2-carboxamide was 16.9 μmol/L. The structure-activity relationships of all compounds are discussed.

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Section: Resultsmentioning

confidence: 99%

Antibacterial and Herbicidal Activity of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides

et al. 2013

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“…37 225 °C). 1 H NMR (400 MHz, DMSO- d 6 ) δ 11.98 (s, 1H), 11.27 (s, 1H), 8.73 (s, 1H), 8.52 (dd, J = 8.0, 1.2 Hz, 1H), 8.00 (d, J = 8.0 Hz, 1H), 7.79 (d, J = 8.4 Hz, 1H), 7.58 (dd, J = 8.0, 1.6 Hz, 1H), 7.54 (t, J = 7.2 Hz, 1H), 7.42 (t, J = 8.4 Hz, 1H), 7.38 (s, 1H), 7.38 (t, J = 9.2 Hz, 1H), 7.20 (t, J = 8.0, Hz, 1H); 13 C NMR (100 MHz, DMSO- d 6 ) δ 163.5, 152.7, 136.0, 135.4, 132.7, 129.4, 129.1, 128.5, 127.9, 127.2, 125.7, 125.2, 124.0, 123.3, 122.6, 120.5, 110.8; HRESI-MS for [C 17 H 12 ClNO 2 −H] − , Calcd 296.0484.…”

Section: Methodsmentioning

confidence: 99%

“…37 248–249 °C). 1 H NMR (400 MHz, DMSO- d 6 ) δ 11.21 (br s, 1H), 10.67 (s, 1H), 8.45 (s, 1H), 7.93 (d, J = 8.0 Hz, 1H), 7.75–7.77 (m, 3H), 7.57 (dd, J = 7.6, 1.6 Hz, 2H), 7.51 (td, J = 8.0, 1.2 Hz, 1H), 7.36 (t, J = 8.0 Hz, 1H), 7.33 (s, 1H); 13 C NMR (100 MHz, DMSO- d 6 ) δ 165.7, 153.5, 138.0, 135.7, 132.0, 131.6, 130.5, 128.7, 128.1, 126.9, 125.8, 123.8, 122.3, 115.7, 110.5; HRESI-MS for [C 17 H 12 BrNO 2 −H] − , Calcd 399.9979.…”

Section: Methodsmentioning

confidence: 99%

Structure–activity relationship studies of naphthol AS-E and its derivatives as anticancer agents by inhibiting CREB-mediated gene transcription

Yamanaka

Xiao

2012

Bioorganic & Medicinal Chemistry

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CREB (cyclic AMP-response element binding protein) is a downstream transcription factor of a multitude of signaling pathways emanating from receptor tyrosine kinases or G-protein coupled receptors. CREB is not activated until it is phosphorylated at Ser133 and its subsequent binding to CREB-binding protein (CBP) through kinase-inducible domain (KID) in CREB and KID-interacting (KIX) domain in CBP. Tumor tissues from various organs present higher level of expression and activation of CREB. Thus CREB has been proposed as a promising cancer drug target. We previously described naphthol AS-E (1a) as a small molecule inhibitor of CREB-mediated gene transcription in living cells. Here we report the structure–activity relationship (SAR) studies of 1a by modifying the appendant phenyl ring. All the compounds were evaluated for in vitro inhibition of KIX–KID interaction, cellular inhibition of CREB-mediated gene transcription and inhibition of proliferation of four cancer cell lines (A549, MCF-7, MDA-MB-231 and MDA-MB-468). SAR indicated that a small and electron-withdrawing group was preferred at the para-position for KIX–KID interaction inhibition. Compound 1a was selected for further biological characterization and it was found that 1a down-regulated the expression of endogenous CREB target genes. Expression of a constitutively active CREB mutant, VP16-CREB in MCF-7 cells rendered the cells resistant to 1a, suggesting that CREB was critical in mediating its anticancer activity. Furthermore, 1a was not toxic to normal human cells. Collectively, these data support that 1a represents a structural template for further development into potential cancer therapeutics with a novel mechanism of action.

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“…Due to the unique biological and pharmacological activity, thiazoles have attracted considerable attention. Various substituted thiazoles have been synthesized and examined for their anti-tubercular, anti-fungal and anti-bacterial activities [16][17][18][19][20][21]. Demonstrations of in vitro activity against the virulent strain of M. tuberculosis, H37Rv is one of the simplest preliminary tests for a new antimycobacterial agent.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of substituted methyl cyclohexanone hybrids for anti-tubercular, anti-bacterial and anti-fungal activity: Facile syntheses under catalysis by ionic liquids

Ghatole¹,

Lanjewar²,

Gaidhane³

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Synthesis of Some New Halogenated N-Thiazolyl Substituted Hydroxy Acid Amides and Their Use as Possible Fungicides

Cited by 15 publications

References 0 publications

Antibacterial and Herbicidal Activity of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides

Antibacterial and Herbicidal Activity of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides

Structure–activity relationship studies of naphthol AS-E and its derivatives as anticancer agents by inhibiting CREB-mediated gene transcription

Evaluation of substituted methyl cyclohexanone hybrids for anti-tubercular, anti-bacterial and anti-fungal activity: Facile syntheses under catalysis by ionic liquids

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