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      Lewis-Acid-Mediated Benzotriazole Ring Cleavage (BtRC) Strategy for the Synthesis of 2-Aryl Benzoxazoles from N-Acylbenzotriazoles†

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      Author(s): , , ,
      Publication date (Electronic):
      Journal: ACS Omega
      Publisher: American Chemical Society

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          Abstract

          A Lewis-acid-mediated ring cleavage of acylbenzotriazoles (RCOBt) followed by cyclization to corresponding benzoxazoles was achieved in good to excellent yields. The reaction was found consistent with the milligram to gram scale.

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          Most cited references22

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          Tafamidis, a potent and selective transthyretin kinetic stabilizer that inhibits the amyloid cascade.

          Christine Bulawa, Stephen Connelly, Michael DeVit … (2012)
          The transthyretin amyloidoses (ATTR) are invariably fatal diseases characterized by progressive neuropathy and/or cardiomyopathy. ATTR are caused by aggregation of transthyretin (TTR), a natively tetrameric protein involved in the transport of thyroxine and the vitamin A-retinol-binding protein complex. Mutations within TTR that cause autosomal dominant forms of disease facilitate tetramer dissociation, monomer misfolding, and aggregation, although wild-type TTR can also form amyloid fibrils in elderly patients. Because tetramer dissociation is the rate-limiting step in TTR amyloidogenesis, targeted therapies have focused on small molecules that kinetically stabilize the tetramer, inhibiting TTR amyloid fibril formation. One such compound, tafamidis meglumine (Fx-1006A), has recently completed Phase II/III trials for the treatment of Transthyretin Type Familial Amyloid Polyneuropathy (TTR-FAP) and demonstrated a slowing of disease progression in patients heterozygous for the V30M TTR mutation. Herein we describe the molecular and structural basis of TTR tetramer stabilization by tafamidis. Tafamidis binds selectively and with negative cooperativity (K(d)s ~2 nM and ~200 nM) to the two normally unoccupied thyroxine-binding sites of the tetramer, and kinetically stabilizes TTR. Patient-derived amyloidogenic variants of TTR, including kinetically and thermodynamically less stable mutants, are also stabilized by tafamidis binding. The crystal structure of tafamidis-bound TTR suggests that binding stabilizes the weaker dimer-dimer interface against dissociation, the rate-limiting step of amyloidogenesis.
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            Copper-catalyzed synthesis of benzoxazoles via a regioselective C-H functionalization/C-O bond formation under an air atmosphere.

            Hideko Nagasawa, Satoshi Ueda (2009)
            An efficient method for the synthesis of functionalized benzoxazoles is described that involves a copper(II)-catalyzed regioselective C-H functionalization/C-O bond formation protocol. The use of dichlorobenzene as a solvent at 160 degrees C allows the use of air as the terminal oxidant in the catalytic synthesis of benzoxazoles in a process that has high functional group tolerance. The presence of a directing group at the meta position markedly improves the reaction efficacy and a variety of 7-substituted benzoxazoles are selectively produced under mild reaction conditions. The mechanism of the reaction is also discussed in this report.
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              Synthesis, structure-activity relationships, and antitumor studies of 2-benzoxazolyl hydrazones derived from alpha-(N)-acyl heteroaromatics.

              Johann Hofmann, K Thies, Johnny Easmon … (2006)
              Recently we have described the antitumor activities of 2-benzoxazolylhydrazones derived from 2-formyl and 2-acetylpyridines. In search of a more efficacious analogue, compounds in which the 2-acetylpyridine moiety has been replaced by 2-acylpyridine and alpha-(N)-acetyldiazine/quinoline groups have been synthesized. The 2-acylpyridyl hydrazones inhibited in vitro cell proliferation in the nM range, whereas the hydrazones derived from the alpha-(N)-acetyldiazines/quinolines inhibited cell growth in the muM range. Compounds tested in the NCI-60 cell assay were effective inhibitors of leukemia, colon, and ovarian cancer cells. E-13k [N-benzoxazol-2-yl-N'-(1-isoquinolin-3-yl-ethylidene)-hydrazine] inhibited the proliferation of MCF-7 breast carcinoma cells more efficiently than nontransformed MCF-10A cells. It is not transported by P-glycoprotein and a weak MRP substrate. Increased concentrations of serum or alpha(1)-acid glycoprotein did not reduce the antiproliferative activity of the compound. In the in vivo hollow fiber assay, E-13k achieved a score of 24, with a net cell kill of OVCAR-3 (ovarian) and SF2-95 (CNS) tumor cells.
              Article 0 comments Cited 25 times – based on 0 reviews     Review now
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                Author and article information

                Journal
                Journal ID (nlm-ta): ACS Omega
                Journal ID (iso-abbrev): ACS Omega
                Journal ID (publisher-id): ao
                Journal ID (coden): acsodf
                Title: ACS Omega
                Publisher: American Chemical Society
                ISSN (Electronic): 2470-1343
                Publication date (Electronic): 28 August 2017
                Publication date Collection: 31 August 2017
                Volume: 2
                Issue: 8
                Pages: 5044-5051
                Affiliations
                [1]Department of Chemistry, Institute of Science, Banaras Hindu University , Varanasi, U.P. 221005, India
                Author notes
                Article
                DOI: 10.1021/acsomega.7b00965
                PMC ID: 6641914
                PubMed ID: 31457781
                SO-VID: 1633d2c1-701a-4a36-a23e-47ebf67cda92
                Copyright © Copyright © 2017 American Chemical Society
                License:

                This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.

                History
                Date received : 10 July 2017
                Date accepted : 14 August 2017
                Categories
                Subject: Article
                Custom metadata
                document-id-old-9 ao7b00965
                document-id-new-14 ao-2017-009652
                ccc-price

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