42404-41-1Relevant academic research and scientific papers
Benzophenone based fluorophore for selective detection of Sn2?+ ion: Experimental and theoretical study
Jadhav, Amol G.,Shinde, Suvidha S.,Lanke, Sandip K.,Sekar, Nagaiyan
, p. 291 - 296 (2017)
Synthesis of novel benzophenone-based chemosensor is presented for the selective sensing of Sn2?+ ion. Screening of competitive metal ions was performed by competitive experiments. The specific cation recognition ability of chemosensor towards
Synthesis, protease inhibition, and antileishmanial activity of new benzoxazoles derived from acetophenone or benzophenone and synthetic precursors
Folquitto, Laís R. S.,Nogueira, Priscila F.,Espuri, Patrícia F.,Gontijo, Vanessa S.,de Souza, Thiago B.,Marques, Marcos J.,Carvalho, Diogo T.,Júdice, Wagner A. S.,Dias, Danielle F.
, p. 1149 - 1159 (2017/05/04)
Abstract: This work reports the synthesis, protease inhibition, and antileishmanial activity of ten benzoxazole derivatives, which were obtained in a three-step synthetic route from 4-hydroxy-acetophenone and 4-hydroxy-benzophenone. These benzoxazoles, the synthetic intermediates, and the starting ketones were evaluated for their inhibitory effect on the activity of cysteine (papain, rCPB2.8, and rCPB3.0) and serine (trypsin) proteases. All compounds showed significant values of IC50 against these enzymes (in the range of 0.0086–0.7612 μM for papain and 0.0075–0.5032 μM for trypsin), being more active than the standard inhibitors (1.7821 and 7.2318 μM, for E64 and TLCK, respectively). Following, all compounds were evaluated in vitro for their leishmanicidal activity against promastigote form of Leishmania amazonensis. The most active compounds were further evaluated against amastigote form and for its toxicity against murine macrophages. The benzoxazole 4d, a benzophenone derivative, and the intermediate 4-hydroxy-3-nitroacetophenone 2b showed significant antileishmanial activity (IC50 = 90.3 μM and IC50 = 130.9 μM, respectively) with selectivity indexes (5.22 and 18.09, respectively) compared to or better than those of two established leishmanicidal drugs, pentamidine (0.58) and amphotericin B (5.31). Graphical Abstract: [InlineMediaObject not available: see fulltext.].
Benzoxazolone Carboxamides as Potent Acid Ceramidase Inhibitors: Synthesis and Structure-Activity Relationship (SAR) Studies
Bach, Anders,Pizzirani, Daniela,Realini, Natalia,Vozella, Valentina,Russo, Debora,Penna, Ilaria,Melzig, Laurin,Scarpelli, Rita,Piomelli, Daniele
, p. 9258 - 9272 (2015/12/23)
Ceramides are lipid-derived intracellular messengers involved in the control of senescence, inflammation, and apoptosis. The cysteine amidase, acid ceramidase (AC), hydrolyzes these substances into sphingosine and fatty acid and, by doing so, regulates their signaling activity. AC inhibitors may be useful in the treatment of pathological conditions, such as cancer, in which ceramide levels are abnormally reduced. Here, we present a systematic SAR investigation of the benzoxazolone carboxamides, a recently described class of AC inhibitors that display high potency and systemic activity in mice. We examined a diverse series of substitutions on both benzoxazolone ring and carboxamide side chain. Several modifications enhanced potency and stability, and one key compound with a balanced activity-stability profile (14) was found to inhibit AC activity in mouse lungs and cerebral cortex after systemic administration. The results expand our arsenal of AC inhibitors, thereby facilitating the use of these compounds as pharmacological tools and their potential development as drug leads.
Unequivocal Preparation of 4- and 5-Acyl-2-aminophenols
Aichaoui, Hocine,Lesieur, Isabelle,Henichart, Jean-Pierre
, p. 679 - 680 (2007/10/02)
Unequivocal methods for the specific preparation of 4- or 5-acyl-2-aminophenols are reported. 5-Acyl-2-aminophenols are obtained by ring opening with dilute sodium hydroxide of 2(3H)-benzoxazolinones acylated at position 6. 4-Acyl-2-aminophenols are obtai
INTERMOLECULAR CHARACTER OF THE REARRANGEMENT OF AMIDES IN POLYPHOSPHORIC ACID
Tseitlin, G.M.,Tokarev, B.V.,Kulagin, V.N.
, p. 931 - 934 (2007/10/02)
When N-benzoyl-o-aminophenol is heated in polyphosphoric acid, both 2-phenylbenzoxazole and 2-phenyl-5-benzoylbenzoxazole are formed, and this shows that the rearrangement of the amides has an intermolecular mechanism.The same mixture is obtained when O,N-dibenzoyl-o-aminophenol is heated under these conditions.The structure of 2-phenyl-5-benzoylbenzoxazole was proved by an alternative synthesis both from p-hydroxybenzophenone through 3-nitro- and 3-benzoylamino-4-hydroxybenzophenone and from 2-phenylbenzoxazole by heating with benzoyl chloride in the presence of zinc oxide.When heated with polyphosphoric acid, benzanilide rearranges to 4-aminobenzophenone; bis(4-benzoylaminophenyl) ether does not undergo rearrangement under these conditions.
