15463-91-9Relevant articles and documents
Development of 2,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one inhibitors of aldehyde dehydrogenase 1A (ALDH1A) as potential adjuncts to ovarian cancer chemotherapy
Buchman, Cameron D.,Buckanovich, Ronald J.,Chtcherbinine, Mikhail,Debnath, Bikash,Felton, Jeremy,Grimley, Edward,Huddle, Brandt C.,Hurley, Thomas D.,Larsen, Scott D.,Li, Siwei,Mao, Shuai,McGonigal, Stacy C.,Neamati, Nouri,Pan, Shu,Sun, Duxin,Takahashi, Cyrus,Wen, Bo
, (2020/12/21)
There is strong evidence that inhibition of one or more Aldehyde Dehydrogenase 1A (ALDH1A) isoforms may be beneficial in chemotherapy-resistant ovarian cancer and other tumor types. While many previous efforts have focused on development of ALDH1A1 select
Ruthenium(II)–Arene Thiocarboxylates: Identification of a Stable Dimer Selectively Cytotoxic to Invasive Breast Cancer Cells
Stephens, Liam J.,Levina, Aviva,Trinh, Iman,Blair, Victoria L.,Werrett, Melissa V.,Lay, Peter A.,Andrews, Philip C.
, p. 1188 - 1200 (2019/12/24)
RuII-arene complexes provide a versatile scaffold for novel anticancer drugs. Seven new RuII-arene-thiocarboxylato dimers were synthesized and characterized. Three of the complexes (2 a, b and 5) showed promising antiproliferative activities in MDA-MB-231 (human invasive breast cancer) cells, and were further tested in a panel of fifteen cancerous and noncancerous cell lines. Complex 5 showed moderate but remarkably selective activity in MDA-MB-231 cells (IC50=39±4 μm Ru). Real-time proliferation studies showed that 5 induced apoptosis in MDA-MB-231 cells but had no effect in A549 (human lung cancer, epithelial) cells. By contrast, 2 a and b showed moderate antiproliferative activity, but no apoptosis, in either cell line. Selective cytotoxicity of 5 in aggressive, mesenchymal-like MDA-MB-231 cells over many common epithelial cancer cell lines (including noninvasive breast cancer MCF-7) makes it an attractive lead compound for the development of specifically antimetastatic Ru complexes with low systemic toxicity.
Sulphide as a leaving group: Highly stereoselective bromination of alkyl phenyl sulphides
Canestrari, Daniele,Cioffi, Caterina,Biancofiore, Ilaria,Lancianesi, Stefano,Ghisu, Lorenza,Ruether, Manuel,O'Brien, John,Adamo, Mauro F.A.,Ibrahim, Hasim
, p. 9042 - 9050 (2019/10/22)
A conceptionally novel nucleophilic substitution approach to synthetically important alkyl bromides is presented. Using molecular bromine (Br2), readily available secondary benzyl and tertiary alkyl phenyl sulphides are converted into the corresponding bromides under exceptionally mild, acid- and base-free reaction conditions. This simple transformation allows the isolation of elimination sensitive benzylic β-bromo carbonyl and nitrile compounds in mostly high yields and purities. Remarkably, protic functionalities such as acids and alcohols are tolerated. Enantioenriched benzylic β-sulphido esters, readily prepared by asymmetric sulpha-Michael addition, produce the corresponding inverted bromides with high stereoselectivities, approaching complete enantiospecificity at -40 °C. Significantly, the reported benzylic β-bromo esters can be stored without racemisation for prolonged periods at -20 °C. Their synthetic potential was demonstrated by the one-pot preparation of γ-azido alcohol (S)-5 in 90% ee. NMR studies revealed an initial formation of a sulphide bromine adduct, which in turn is in equilibrium with a postulated dibromosulphurane intermediate that undergoes C-Br bond formation.
Ring expansion-annulation strategy for the synthesis of substituted azulenes and oligoazulenes. 2. Synthesis of azulenyl halides, sulfonates, and azulenylmetal compounds and their application in transition-metal-mediated coupling reactions
Crombie, Aimee L.,Kane Jr., John L.,Shea, Kevin M.,Danheiser, Rick L.
, p. 8652 - 8667 (2007/10/03)
A "ring expansion-annulation strategy" for the synthesis of substituted azulenes is described based on the reaction of β'-bromo- α-diazo ketones with rhodium carboxylates. The key transformation involves an intramolecular Buechner reaction followed by β-elimination of bromide, tautomerization, and in situ trapping of the resulting 1-hydroxyazulene as a carboxylate or triflate ester. Further synthetic elaboration of the azulenyl halide and sulfonate annulation products can be achieved by employing Heck, Negishi, Stille, and Suzuki coupling reactions. Reaction of the azulenyl triflate 84 with pinacolborane provides access to the azulenylboronate 91, which participates in Suzuki coupling reactions with alkenyl and aryl iodides. The application of these coupling reactions to the synthesis of biazulenes, terazulene 101, and related oligoazulenes is described, as well as the preparation of the azulenyl amino acid derivative 110.
Anti-viral compounds
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, (2008/06/13)
The present invention relates to compounds of Formula (I) below, which inhibit the growth of picornaviruses, Hepatitus viruses, enteroviruses, cardioviruses, polioviruses, coxsackieviruses of the A and B groups, echo virus and Mengo virus. wherein: A is phenyl, pyridyl, substituted phenyl, substituted pyridyl, or benzyl; R is hydrogen, COR4, or COCF3; X is N—OH, O, or CHR1; R1is hydrogen, halo, CN, C1-C4alkyl, —C≡CH, CO(C1-C4alkyl), CO2(C1-C4alkyl), or CONR2R3; R2and R3are independently hydrogen or C1-C4alkyl; A′ is hydrogen, halo, C1-C6alkyl, benzyl, naphthyl, thienyl, furyl, pyridyl, pyrollyl, COR4, S(O)nR4, or a group of the formula R4is C1-C6alkyl, phenyl, or substituted phenyl; n is 0, 1, or 2; R5is independently at each occurrence hydrogen or halo; m is 1, 2, 3, or 4; and R6is hydrogen, halo, CF3, OH, CO2H, NH2, NO2, CONHOCH3, C1-C4alkyl, or CO2(C1-C4alkyl), C1-C4alkoxy; or a pharmaceutically acceptable salt thereof.
A ring expansion-annulation strategy for the synthesis of substituted azulenes. Preparation and suzuki coupling reactions of 1-azulenyl triflates
John L Jr., Kane,Shea, Kevin M.,Crombie, Aimee L.,Danheiser, Rick L.
, p. 1081 - 1084 (2007/10/03)
(matrix presented) A new strategy for the synthesis of substituted azulenes is reported, based on the reaction of β′-bromo-α-diazo ketones with rhodium carboxylates The key transformation involves intramolecular addition of a rhodium carbenoid to an arene π-bond, electrocyclic ring opening, β-elimination, tautomerization, and trapping to produce 1-hydroxyazulene derivatives. The synthetic utility of the method is enhanced by the ability of the triflate derivatives to participate in Suzuki coupling reactions, as illustrated in a synthesis of the antiulcer drug egualen sodium (KT1-32).
Novel azo derivatives as prodrugs of 5-aminosalicylic acid and amino derivatives with potent platelet activating factor antagonist activity
Carceller,Salas,Merlos,Giral,Ferrando,Escamilla,Ramis,García-Rafanell,Forn
, p. 3001 - 3013 (2007/10/03)
This paper describes the synthesis of a series of azo compounds able to deliver 5-aminosalicylic acid (5-ASA) and a potent platelet activating factor (PAF) antagonist in a colon-specific manner for the purpose of treating ulcerative colitis. We found it p
Synthesis and properties of germa-γ-lactones
Kakimoto, Norihiro,Yoshiwara, Tohru,Akiba, Mitsuo,Ishido, Yoshiharu
, p. 247 - 254 (2007/10/02)
Trialkylgermylpropanoic acids treated with 1 mole of bromine afford the monobromopropanoic acids, which are converted into the corresponding germa-γ-lactones in good yields by hydrolysis.The physical, chemical, and biological properties of these compounds are described.
Reactions of Carboxylic Acid Derivatives with Superoxide
Forrester, Alexander R.,Purushotham, Vemeshetti
, p. 945 - 951 (2007/10/02)
The mechanisms of the reactions of superoxide with carboxylic esters, acyl peroxides, and the acyl chlorides of α- and β-bromocarboxylic acids have been investigated.Experimental evidence is presented supporting the view that (a) conversion of an ester into its carboxylic acid does not proceed via the corresponding acyl peroxide; (b) conversion of acyl peroxide into carboxylic acid by superoxide involves either electron transfer to or an SN2 reaction on the peroxidic group; (c) α-bromoacyl chlorides with superoxide give the corresponding aldehyde via a cyclic peroxidic intermediate.
Phenylmercaptotetrazolo- and nitroindazolo masked development/image modifiers
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, (2008/06/13)
Novel nitrobenzyl compounds are incorporated into a photographic emulsion or developer for controlled release of development/image modifier compounds. This occurs imagewise only after developer oxidation products have been formed in the course of the development process. For example, nitrobenzyl-masked phenylmercaptotetrazole (PMT), incorporated into a silver halide emulsion, reacts with developer oxidation products via an electron transfer mechanism to release the potent development restrainer PMT.
