5768-39-8

Usage

Synthesis Reference(s)

Tetrahedron Letters, 17, p. 3361, 1976 DOI: 10.1016/S0040-4039(00)93045-4

InChI:InChI=1/C17H14BrN3O2/c18-13-6-7-15-14(8-13)12(9-19-15)10-20-21-17(23)16(22)11-4-2-1-3-5-11/h1-10,16,20,22H,(H,21,23)/b12-10-

Upstream product

• 75-11-6 diiodomethane 
• 303-38-8 2,3-Dihydroxybenzoic acid 
• 254973-61-0 benzo[d][1,3]dioxol-5-yl(trimethylsilyl)methanone 
• 274-09-9 Methylenedioxybenzene 
• 124-38-9 carbon dioxide 
• 33842-16-9 benzo[1,3]dioxole-4-carboxylic acid methyl ester 
• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 23158-06-7 benzo[1,3]dioxole-4-carboxylic acid ethyl ester 
• 769-30-2 benzo[1,3]dioxol-4-yl-methanol 
• 1521-38-6 2,3-dimethoxybenzoic acid 
• 7797-83-3 2H-benzo[d]1,3-dioxolane-4-carbaldehyde 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 2411-83-8 methyl-2,3-dihydroxybenzoate 

Downstream Products

• 33842-16-9 benzo[1,3]dioxole-4-carboxylic acid methyl ester 
• 66411-55-0 2,3-(Methylenedioxy)benzoyl chloride 
• 97174-59-9 N,N'-di-(1,3-benzodioxol-4-yl)urea 
• 111081-10-8 tert-butyl [2,3-(methylenedioxy)phenyl]carbamate 
• 69151-39-9 NU 1034 
• 1668-84-4 benzo[d][1,3]dioxol-4-amine 
• 482-32-6 kokusagine 
• 112885-30-0 2,3-methylenedioxy-N-[(4-benzyl-2-morpholinyl)methyl]benzamide 
• 7797-83-3 2H-benzo[d]1,3-dioxolane-4-carbaldehyde 
• 769-30-2 benzo[1,3]dioxol-4-yl-methanol 
• 161886-19-7 benzo[1,3]dioxole-4-carbonitrile 
• 38489-70-2 2,3-(methylenedioxy)cinnamic acid 
• 198554-04-0 4-[1-(1,3-benzodioxol-4-ylcarbonyl)piperidin-4-yl]-6-(4-methoxybenzyl)pyrimidin-2-amine 
• 1137558-08-7 benzyl benzo[d][1,3]dioxol-4-ylcarbamate 

Relevant academic research and scientific papers

Synthesis of 2,3-dihydrobenzo[b][1,4]dioxine-5-carboxamide and 3-oxo-3,4-dihydrobenzo[b][1,4]oxazine-8-carboxamide derivatives as PARP1 inhibitors

Poly(ADP-ribose) polymerase 1 (PARP1), a widely explored anticancer drug target, plays an important role in single-strand DNA break repair processes. High-throughput virtual screening (HTVS) of a Maybridge small molecule library using the PARP1-benzimidazole-4-carboxamide co-crystal structure and pharmacophore model led to the identification of eleven compounds. These compounds were evaluated using recombinant PARP1 enzyme assay that resulted in the acquisition of three PARP1 inhibitors: 3 (IC50 = 12 μM), 4 (IC50 = 5.8 μM), and 10 (IC50 = 0.88 μM). Compound 4 (2,3-dihydro-1,4-benzodioxine-5-carboxamide) was selected as a lead and was subjected to further chemical modifications, involving analogue synthesis and scaffold hopping. These efforts led to the identification of (Z)-2-(4-hydroxybenzylidene)-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxamide (49, IC50 = 0.082 μM) as the most potent inhibitor of PARP1 from the series.

A heterocyclic compound and use thereof

The invention discloses a compound of a general formula I and application of the compound serving as a plant disease-resistance activator. In the formula, a substituent group R1 and 0-3 substituent groups R2 exist on the 4th, 5th, 6th and 7th sites; R1 is independently selected from -R3OOH, -R4OOR5, -R6OH and -R7-O-R8; R2 is independently selected from C1-C6 alkyl, C1-6 halogenated alkyl, C1-C6 alkoxy, C1-C6 halogenated alkoxy, hydroxyl, halogen, nitro, amino and C1-C6 alkylamino; R3, R4, R5, R6, R7 and R8 are independently selected from C1-C6 alkyl and C1-6 halogenated alkyl. The compound induces plants to generate disease resistance so as to inhibit pathogens instead of directly killing or inhibiting the pathogens. The compound has the advantages of systematicness, durability, broad spectrum, high safety and the like, so the amount of highly toxic pesticides can be reduced, and the compound is environmentally friendly and has huge industrialized and commercial prospects and market values.

4-Alkyliden-azetidinones modified with plant derived polyphenols: Antibacterial and antioxidant properties

Antimicrobial resistance is one of the major and growing concerns in hospital- and community acquired infections, and new antimicrobial agents are therefore urgently required. It was reported that oxidative stress could contribute to the selection of resistant bacterial strains, since reactive oxygen species (ROS) revealed to be an essential driving force. In the present work 4-alkylidene-azetidinones, a new class of antibacterial agents, were functionalized with phytochemical polyphenolic acids such as protocatechuic, piperonyl, caffeic, ferulic, or sinapic acids and investigated as dual target antibacterial-antioxidant compounds. The best candidates showed good activities against multidrug resistant clinical isolates of MRSA (MICs 2–8 μg/mL). Among the new compounds, two revealed the best antioxidant capacity with TEAC-DPPH and TEAC-ABTS being significantly more active than Trolox.

Platinum nanoparticles supported on polymeric ionic liquid functionalized magnetic silica: effective and reusable heterogeneous catalysts for the selective oxidation of alcohols in water

In this research, the syntheses of core-shell magnetic silica nanostructures, functionalized by a polymeric ionic liquid and immobilization of platinum nanoparticles, are described. Firstly, the magnetic silica nanoparticles were synthesized and modified using an amine-containing organosilane through a single-step process. The synthesized nanostructures were functionalized by the synthesis and polymerization of a pyridinium ionic liquid and a methyl methacrylate monomer, respectively, onto their surfaces. The platinum nanoparticles were immobilized on the functionalized nanoparticles. The obtained functionalized nanostructures have been used in the selective aerobic oxidation, in an aqueous medium, of primary and encumbered secondary aliphatic alcohols, and exhibit high activity at mild temperatures.

SULFONYLUREAS AND RELATED COMPOUNDS AND USE OF SAME

ABSTRACT The present invention provides for certain sulfonyl ureas and related compounds which have advantageous properties and show useful activity in the inhibition of activation of the NLRP3 inflammasome. Such compounds are useful in the treatment of a wide range of disorders in which the inflammation process, or more specifically the NLRP3 inflammasome, have been implicated as being a key factor.

SYNTHESIS AND ANTICANCER ACTIVITY OF ARYL AND HETEROARYL-QUINOLIN DERIVATIVES

A compound of Formula I is disclosed as follows: or a pharmaceutically acceptable salt, prodrug, solvate, or metabolite thereof, wherein R is hydrogen, P(═O)(OH)2, P(═O)(O(C1-C18)alkylene(C6-C20)aryl)2, P(═O)(OH)(OM), P(═O)(OM)2, P═O(O2M), S(═O)(OH)2, S(═O)(O(C1-C18)alkylene(C6-C20)aryl)2, S(═O)(OH)(OM), S(═O)(OM)2; M is a monovalent or divalent metal ion, or alkylammonium ion; W is (C6-C20)aryl, (C6-C20)heteroaryl, (C1-C18)alkyl(C6-C20)aryl, (C1-C18)alkyl(C6-C20)heteroaryl, hydroxy(C6-C20)aryl, hydroxy(C6-C20)heteroaryl, (C1-C18)alkoxy(C6-C20)aryl, (C1-C18)alkoxy(C6-C20)heteroaryl, (C1-C18)alkylenedioxy(C6-C20)aryl, (C1-C18)alkylenedioxy(C6-C20)heteroaryl, halo(C6-C20)aryl, halo(C6-C20)heteroaryl, (C1-C18)alkylamino(C6-C20)aryl, (C1-C18)alkylamino(C6-C20)heteroaryl, (C1-C18)cycloalkylamino(C6-C20)aryl, or (C1-C18)cycloalkylamino(C6-C20)heteroaryl, and their OR8 substutes; R5 is (C1-C18alkoxy, hydrogen, hydroxyl, O—(C1-C18)alkyl(C6-C20)aryl, halo or OR8, or R5 and R6 are (C1-C18)dioxy provided that R7 is hydrogen; R6 is hydroxyl, O—(C1-C18)alkyl(C6-C20)aryl, halo or ORR, (C1-C18)alkoxy, (C1-C18)alkylamino, or (C1-C18)cycloalkylamino, or R6 and R7 are (C1-C18)dioxy provided that R5 is hydrogen; R7 is hydrogen, halo or OR8, hydroxyl, or O—(C1-C18)alkyl(C6-C20)aryl; and R8 is P(═O)(OH)2, P(═O)(O(C1-C18)alkyl(C6-C20)aryl)2, P(═O)(OH)(OM), or P(═O)(OM)2, P═O(O2M).

Synthesis, crystal structures, insecticidal activities, and structure-activity relationships of novel N ′- Tert -Butyl- N ′-substituted-benzoyl- N -[di(octa)hydro]benzofuran{(2,3-dihydro)benzo[1, 3]([1,4])dioxine}carbohydrazide derivatives

Several series of novel N′-tert-butyl-N′-substituted-benzoyl-N- [di(octa)hydro]benzofuran{(2,3-dihydro)benzo[1,3]([1,4])dioxine}carbohydrazide derivatives Ia, Ib, IIa-IIg, IIIa, IIIb, and Va-Vc were designed and synthesized. Their structures were confirmed by 1H NMR spectra, HRMS, and X-ray single-crystal structures. The larvicidal activities against oriental armyworm, beet armyworm, diamond-back moth, and corn borer of these compounds were evaluated and contrasted with those of RH-2485, JS-118, and ANS-118. The larvicidal activities against oriental armyworm indicate that monosubstituent or multisubstituents and the substituting group position cannot promote increasing activities and that the cycle region in the general structure of IIa-IIg is much more sensitive to activity than that in the general structure of Ia and Ib. The space volume of the A ring in the structure of Va cannot be too large; if it is, the activity will be decreased significantly. Stomach toxicities against beet armyworm, diamond-back moth, and corn borer of compounds Ia, Ib and IIg indicate that benzoheterocyclic analogues of N-tert-butyl-N,N′- diacylhydrazines show significant selectivities to different lepidopterous pests.

Synthesis of carbon-11-labeled casimiroin analogues as new potential PET agents for imaging of quinone reductase 2 and aromatase expression in breast cancer

Carbon-11-labeled casimiroin analogues were first designed and synthesized as new potential PET agents for imaging of quinone reductase (QR) 2 and aromatase expression in breast cancer. [11C]casimiroin (6-[ 11C]methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one, [ 11C]11) and its carbon-11-labeled analogues 5,6,8-trimethoxy-1-[ 11C]methyl-4-methylquinolin-2(1H)-one ([11C]17), 8-methoxy-1-[11C]methyl-4-methylquinolin-2(1H)-one ([ 11C]21a), 6,8-dimethoxy-1-[11C]methyl-4-methylquinolin- 2(1H)-one ([11C]21b), and 5,8-dimethoxy-1-[11C]methyl-4- methylquinolin-2(1H)-one ([11C]21c), were prepared from their corresponding precursors with [11C]methyl triflate ([ 11C]CH3OTf) under basic conditions (NaH) through either O- or N-[11C]methylation and isolated by semi-preparative HPLC method in 40-50% radiochemical yields decay corrected to end of bombardment (EOB), based on [11C]CO2, and 111-185 GBq/μmol specific activity at the end of synthesis (EOS).

CONDENSED TETRAHYDROQUINOLINE DERIVATIVE AND USE THEREOF FOR MEDICAL PURPOSES

The problem of the present invention is to provide a compound having a GR selective binding activity, which shows less action on other nuclear receptors such as progesterone receptor (PR), mineralocorticoid receptor (MR) and the like. The present invention provides a condensed tetrahydroquinoline compound represented by the following formula (I) wherein each symbol is as defined in the present specification, or a pharmaceutically acceptable salt thereof or a hydrate thereof.

Quinazoline derivatives

The invention concerns quinazoline derivatives of Formula (I) wherein each of m, R1, n, R2 and R3 have any of the meanings defined in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an anti-invasive agent in the containment and/or treatment of solid tumour disease.