2199-92-0

Upstream product

• 90-59-5 3,5-Dibromosalicylaldehyde 
• 141-97-9 ethyl acetoacetate 
• 5977-14-0 acetoacetamido 
• 3147-55-5 3,5-dibromosalicylic acid 
• 105-45-3 acetoacetic acid methyl ester 

Downstream Products

• 108222-33-9 3-[2-(phenylamino)thiazol-4-yl]-6,8-dibromo-2H-chromen-2-one 
• 106578-20-5 6,8-dibromo-3-(2-bromoacetyl)-2H-chromen-2-one 
• 116317-11-4 6,8-Dibromo-3-{2-[3-(2-hydroxy-phenyl)-5-phenyl-pyrazol-1-yl]-thiazol-4-yl}-chromen-2-one 
• 181126-00-1 4-[4-(6,8-dibromo-2-oxo-2H-chromen-3-yl)-thiazol-2-ylamino]-benzenesulfonamide 
• 106578-12-5 6,8-Dibromo-3-(2-phenyl-thiazol-4-yl)-chromen-2-one 
• 108255-32-9 N-[4-(6,8-Dibromo-2-oxo-2H-chromen-3-yl)-thiazol-2-yl]-N-phenyl-acetamide 
• 1215211-09-8 C₂₆H₁₈Br₂N₄O₃ 
• 1260653-68-6 C₂₅H₁₅Br₂FN₄O₂ 
• 219621-22-4 C₁₇H₁₂Br₂N₂O₂ 
• 1375188-15-0 3-(6,8-dibromo-2-oxo-2H-chromen-3-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde 
• 1375188-30-9 5-((3-(6,8-dibromo-2-oxo-2H-chromene-3-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1375188-22-9 5-((3-(6,8-dibromo-2-oxo-2H-chromene-3-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)dihydrothioxopyrimidine-4,6(1H,5H)-dione 
• 1365411-61-5 C₂₅H₁₅Br₂ClN₄O₂ 

Relevant academic research and scientific papers

Synthesis of novel triheterocyclic thiazoles as anti-inflammatory and analgesic agents

Triheterocyclic thiazoles containing coumarin and carbostyril (1-aza coumarin) have been synthesized by the reaction of the in situ generated 4-thioureidomethyl carbostyril and 3-bromoacetyl coumarins. The new compounds have been tested for their in vivo analgesic and anti-inflammatory activities. Qualitative SAR studies indicate that, the chloro substitution at C-7 in carbostyril and 6,8-dibromo substitution in the coumarin ring enhance anti-inflammatory activity. These compounds were also found to provide significant protection against acetic acid writhing in animal models. All the compounds have been characterized by IR, 1H NMR, 13C NMR and mass spectrometry.

A facile one pot multi component synthesis of alkyl 4-oxo-coumarinyl ethylidene hydrazono-thiazolidin-5-ylidene acetates and their antiviral activity

An efficient one-pot synthesis of alkyl 4-oxo-coumarinyl ethylidene hydrazono-thiazolidin-5-ylidene acetate derivatives has successfully been achieved via a three component cyclization reaction of various substituted 3-acetyl coumarins, thiosemicarbazide and dialkyl acetylenedicarboxylates, in presence of acetic acid. The isolated products were obtained in pure form with high yields through simple workup. The newly synthesised compounds structure was established on the basis of spectral (IR, 1H NMR, 13C NMR, ESI- mass) elemental analysis and single crystal X-ray data. All synthesised compounds were screened for their antiviral activity against a broad spectrum of human viruses in different cell cultures. Of the novel synthesised compounds, thirteen compounds exerted activity against Punta Toro virus, including compound IV-19, for which an antiviral potency was noted against a broad panel of DNA and RNA viruses as well.

Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives

Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory activities of these new compounds are tested by Ellman’s method. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(6-nitrocoumarinyl)-1,3-thiazole-2-amine showed the best activity with an in vitro AChE inhibitory rate of 58% and an IC50 value of 12 ± 0.38 μg/mL.

Synthesis and antiproliferative evaluation of novel biheterocycles based on coumarin and 2-aminoselenophene-3-carbonitrile unit

A series of novel coumarins with 2-amino-3-cyanoselenophen-5-yl unit on C-3 have been synthesized. These compounds prepared easily at room temperature, in a short time and in high yield. The importance of biheterocyclic units as dominant structural motif of coumarin derivatives has been well recognized. Anti-cancer activity screening on MCF-7 cell line allowed identification of 2-amino-5-(6-bromo-2-oxo-2H-chromen-3-yl)selenophene-3-carbonitrile with the highest level of cytotoxic activity with mean IC50 and cLogP (partition co-efficient) values 10.84 μM and 3.18, respectively. The most radical scavenging compound was also recognized. Graphic abstract: [Figure not available: see fulltext.].

The effects of bromine atoms on the photophysical and photochemical properties of 3-cinnamoylcoumarin derivatives

Eight coumarin derivatives (T1-T8) with or without modification using one or two bromine atoms were synthesized through the aldol condensation reaction. Their photophysical, photochemical and electrochemical properties were investigated. It was shown that

Copper(I)-promoted cycloalkylation-peroxidation of unactivated alkenes via sp3 C-H functionalisation

A copper(i)-promoted cycloalkylation-peroxidation strategy has been developed via a three-component reaction involving cycloalkanes, tert-butyl hydroperoxide (TBHP) and internal conjugated alkenes possessing electron-withdrawing groups (EWGs). This process installs C-O and C-C bonds via sp3 C-H functionalisation with concomitant generation of two stereocentres. This regioselective radical addition of coumarin system is opposite to that of styrene.

One-pot multicomponent synthesis of indole incorporated thiazolylcoumarins and their antibacterial, anticancer and DNA cleavage studies

A series of indole incorporated thiazolylcoumarins (7a-q) have been synthesized and evaluated for their antibacterial, anticancer and DNA cleavage studies. Analysis of antibacterial studies indicated that all the synthesized compounds possess promising activity towards the screened bacterial strains. In vitro anticancerous action was studied for compound 7a (NSC: 768621/1) against the full panel of 60 human tumor cell lines. The five dose level activity results revealed that, the compound 7a was active against all the cell lines among them it has shown potent activity against Leukemia: CCRF-CEM (GI50: 0.33 μM), Non-Small Cell Lung Cancer: NCI-H522 (GI50: 1.03 μM), Colon Cancer: HCT-116 (GI50: 1.60 μM), CNS Cancer: SF-539 (GI50: 1.58 μM), Melanoma MALME-3M (GI50: 1.59 μM), Ovarian Cancer: OVCAR-3 (GI50: 1.16 μM), Renal Cancer: UO-31 (GI50: 0.76 μM), Prostate Cancer: PC-3 (GI50: 0.82 μM) and Breast Cancer: BT-549 (GI50: 1.13 μM). DNA cleavage studies revealed that even at 50 μg/mL concentration complete DNA digestion was observed for all the compounds, except for compound (7o) where partial DNA digestion was observed even at 100 μg/mL.

Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives

Several 3-carbonyl (1-26), 3-acyl (27-52), and 3-carboxyhydrazido (53-58) coumarins have been synthesized in high yields (72-99%) and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Different substituents on the coumarin nucleus were evaluated for their effect on biological activity and isoform selectivity. Substitution at position C7 of the 3-ethyl ester coumarin ring, or the introduction of a hydrazido substituent at C3, were important to obtain highly potent and selective hMAO-B inhibitors with IC50 values in the nanomolar range. Some derivatives were also submitted to a stability test and showed no chemical cleavage in vitro.

2-Hydroxy-2-methyl-2H-1-benzopyran-3-carboxamide Derivatives

The reaction of 2-hydroxybenzaldehydes with 3-oxobutanamide affords 2,4-dihydroxy-2-methyl-2H-3,4-dihydro-1-benzopyran-3-carboxamides and 2-hydroxy-2-methyl-2H-1-benzopyran-3-carboxamides, depending on the particular aldehyde and the experimental conditions used.