107144-91-2Relevant articles and documents
Synthesis of 7-Azido-3-Formylcoumarin – A Key Precursor in Bioorthogonally Applicable Fluorogenic Dye Synthesis
Pünk?sti, Zoltán,Kele, Péter,Herner, András
supporting information, p. 1183 - 1188 (2018/03/21)
Coumarins represent an important group of natural products and a common part of various drugs and fluorescent dyestuffs. Herein, we present the synthesis of a coumarin that can serve as a key starting material in the design and synthesis of bioorthogonally applicable fluorogenic dyes. The synthesis of 7-azido-3-formylcoumarin started from 7-diallylaminocoumarin. This allyl protected aminocoumarin is otherwise hard to obtain by conventional methods but was conveniently accessed in good yields by a sequential, Wittig-reaction–UV isomerization process. This sequential approach was studied in more details and applied for the synthesis of a series of substituted coumarins even in one-pot.
Coumarin carboxylic acids as monocarboxylate transporter 1 inhibitors: In vitro and in vivo studies as potential anticancer agents
Gurrapu, Shirisha,Jonnalagadda, Sravan K.,Alam, Mohammad A.,Ronayne, Conor T.,Nelson, Grady L.,Solano, Lucas N.,Lueth, Erica A.,Drewes, Lester R.,Mereddy, Venkatram R.
, p. 3282 - 3286 (2016/07/12)
Novel N,N-dialkyl carboxy coumarins have been synthesized as potential anticancer agents via inhibition of monocarboxylate transporter 1 (MCT1). These coumarin carboxylic acids have been evaluated for their in vitro MCT1 inhibition, MTT cancer cell viability, bidirectional Caco-2 cell permeability, and stability in human and liver microsomes. These results indicate that one of the lead candidate compounds 4a has good absorption, metabolic stability, and a low drug efflux ratio. Systemic toxicity studies with lead compound 4a in healthy mice demonstrate that this inhibitor is well tolerated based on zero animal mortality and normal body weight gains compared to the control group. In vivo tumor growth inhibition studies in mice show that the candidate compound 4a exhibits significant single agent activity in MCT1 expressing GL261-luc2 syngraft model but doesn't show significant activity in MCT4 expressing MDA-MB-231 xenograft model, indicating the selectivity of 4a for MCT1 expressing tumors.
3-substituted anilines as scaffolds for the construction of glutamine synthetase and DXP-reductoisomerase inhibitors
Mutorwa, Marius,Salisu, Sheriff,Blatch, Gregory L.,Kenyon, Colin,Kaye, Perry T.
experimental part, p. 2723 - 2736 (2009/12/09)
Access to a series of truncated ATP analogs, as potential anti-tuberculosis agents, has been explored via alkylation and acylation of 3-aminophenol, whereas chloroacetylation, using chloroacetyl chloride, and subsequent Arbuzov phosphonation of a series of 3-substituted anilines have afforded a series of phosphonate derivatives as potential antimalarial agents.
Production of aminophenols
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, (2008/06/13)
A method of producing N,N-disubstituted aminophenols of the general formula STR1 wherein R1 and R2 are the same or different and each represents a saturated or unsaturated aliphatic hydrocarbyl, cycloalkyl, aralkyl, the phenyl ring of which may be further substituted, alkoxyalkyl, or a cycloalkylalkyl, except that R1 and R2 are not simultaneously methyl and R' represents hydrogen, halogen, nitro, cyano, alkyl or alkoxy, which comprises reacting an aminophenol of general formula STR2 wherein R3 represents hydrogen or R1, and R' is as defined above, with an organic halide species of general formula R2 X wherein R2 is as defined above and X is halogen under aqueous acidic conditions with the periodic addition of an acid trapping agent in such a way that continuous monitoring of pH is not required.
Organosilicon polymers, and dyes, exhibiting nonlinear optical response
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, (2008/06/13)
Organosilicon polymers, including crosslinked polymers and crosslinkable prepolymers, of cyclic polysiloxane, organic dyes, and, optionally, polyenes. The dyes include those with delocalized Pi electron systems linking electron donor groups and electron acceptor groups, and with at least two carbon-carbon double bond-containing pendant groups attached to at least two different sites from among the indicated delocalized Pi electron systems, donor groups, and acceptor groups.
