- A novel method for the synthesis of oxazolocoumarin derivatives
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Anodic oxidation of 7-hydroxycoumarin derivatives 1a-f in anhyd acetonitrile-lithium perchlorate at constant potential between 1.70-1.80 V (vs. Ag/10-2 M Ag+) using an undivided cell and platinium gauze electrodes leads to the formation of the corresponding oxazolocoumarin derivatives 2 and/or 3 according to the position of the second OH group in the benzene ring of the coumarin derivatives 1e,f. The formation of these oxidation products is discussed.
- Abdelghani, Essam,El-Aal, Ali Abd,Shehab, Wesam,El-Mobayed, Medhat
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Read Online
- Benzoxazole compound and application thereof
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The invention belongs to the field of medical treatment, and particularly relates to a benzoxazole compound and application thereof, wherein the benzoxazole compound has a compound structure as represented by a formula (A), and the compound can be used fo
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Paragraph 0063; 0064; 0066
(2020/07/06)
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- Multicatalytic Beckmann rearrangement of 2-hydroxylarylketone oxime: Switchable synthesis of benzo[d]oxazoles and N-(2-hydroxylaryl)amides
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A switchable synthesis route is developed for benzo[d]oxazole derivatives and (2-hydroxylaryl)benzamide from 2-hydroxylbenzeneketoxime using organomolecules (BOP-Cl, and CNC) and Lewis acid cocatalyzed Beckmann rearrangement (BR) reaction. Further, this reaction is switched using different organocatalysts.
- Li, Zhen,Fang, Chengtao,Zheng, Yannan,Qiu, Guanyinsheng,Li, Xiaofang,Zhou, Hongwei
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p. 3934 - 3937
(2018/10/02)
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- Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles
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The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.
- Nimnual, Phongprapan,Tummatorn, Jumreang,Thongsornkleeb, Charnsak,Ruchirawat, Somsak
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p. 8657 - 8667
(2015/09/15)
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- IRE-1α INHIBITORS
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PROBLEM TO BE SOLVED: To provide compounds which directly inhibit inositol requiring enzyme 1 (IRE-1α activity) in vitro, prodrugs, and pharmaceutically acceptable salts thereof. SOLUTION: The present invention provides a compound represented by formula (A) [R3 and R4 are H or the like; Q5-Q8, together with the benzene ring to which they are attached, form a benzofused ring, where at least one of Q5-Q8 is a heteroatom selected from N, O, and S. COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 1374; 1376; 1377
(2016/10/07)
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- One-pot synthesis of benzoxazoles via the metal-free ortho-C-H functionalization of phenols with nitroalkanes
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PPA-activated nitroalkanes are employed in the design of a one-pot cascade transformation involving metal-free and oxidant-free direct ortho-C-H functionalization, followed by Beckman rearrangement and intramolecular cyclocondensation to produce benzoxazoles and benzobisoxazoles directly from easily available phenols.
- Aksenov, Nicolai A.,Aksenov, Alexander V.,Nadein, Oleg N.,Aksenov, Dmitrii A.,Smirnov, Alexander N.,Rubin, Michael
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p. 71620 - 71626
(2015/09/08)
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- Development of a multikilogram synthesis of a chiral epoxide precursor to a CCR1 antagonist. Use of in situ monitoring for informed optimisation via fragile intermediates
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The optimisation and scale up of a manufacturing route to a key intermediate, acetic acid 4-acetylamino-3-(2-methyl-oxiranyl- methoxy)phenyl ester (2), utilising a SNAr coupling, the hydro- genation of a nitro moiety and the conversion of a chi
- Ange, Debra,Booker, James E. M.,Pedge, Nicholas,Sinclair, Rhona,Sleigh, Chris,Stefinovic, Marijan,Vaz, Luis-Manuel,Way, Edward
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scheme or table
p. 72 - 84
(2010/05/02)
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- Efficient synthesis of 2-substituted benzoxazoles via Beckmann rearrangement of 2-hydroxyaryl ketoximes using diethyl chlorophosphate
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An efficient method for synthesis of 2-substituted benzoxazoles has been developed using diethyl chlorophosphate. 2-Hydroxyaryl ketoximes are efficiently converted to benzoxazoles by heating in the presence of diethyl chlorophosphate via Beckmann rearrangement of ketoxime in excellent yields. This method avoids the use of strong acids, harsh conditions, and long reaction times. Georg Thieme Verlag Stuttgart.
- Sardarian,Shahsavari-Fard
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experimental part
p. 1391 - 1393
(2009/04/06)
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- CYANOISOQUINOLINE COMPOUNDS AND METHODS OF USE THEREOF
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The present invention relates to cyanoisoquinoline compounds suitable for use in treating hypoxia inducible factor-mediated and/or erythropoietin-associated conditions. The cyanoisoquinoline compounds of the invention have the following structure: Formula (I).
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Page/Page column 92
(2008/06/13)
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- NOVEL TRICYCLIC SPIRODERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
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The invention provides compounds of formula (I) wherein m, R1, n, R2, q, p, X, Y, R3, R4, t and, R5 are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.
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Page/Page column 41
(2008/06/13)
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- NOVEL TRICYCLIC SPIRODERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
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The invention provides compounds of formula (I) wherein m, R1, n, R2, q, X, Y, Z, R3, R4, R5, R6, R7, R8, t and R9 are as defined in the specification, proc
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Page/Page column 35
(2010/02/11)
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- 2-Ethoxybenzoxazole as a bioisosteric replacement of an ethyl benzoate group in a human rhinovirus (HRV) capsid binder
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A series of pyridazinylpiperidinyl capsid-binding compounds with novel bicyclic substituents were synthesized and screened against human rhinovirus (HRV). Several 2-alkoxy- and 2-alkylthio-benzoxazole and benzothiazole derivatives showed excellent anti-HRV activity. When tested against a panel of 16 representative HRV types the 2-ethoxybenzoxazole derivative 13 was found to have superior HRV activity (median EC50 3.88 ng/mL) to known capsid-binders Pleconaril and Pirodavir. Compound 13 illustrates that a 2-alkoxybenzoxazole group can be an effective bioisostere for a benzoate ester or benzaldehyde oxime ether functionality.
- Brown, Renee N.,Cameron, Rachel,Chalmers, David K.,Hamilton, Stephanie,Luttick, Angela,Krippner, Guy Y.,McConnell, Darryl B.,Nearn, Roland,Stanislawski, Pauline C.,Tucker, Simon P.,Watson, Keith G.
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p. 2051 - 2055
(2007/10/03)
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- NOVEL TRICYCLIC SPIROPIPERIDINES OR SPIROPYRROLIDINES
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The invention provides compounds of formula (I) wherein m, R1, n, R2, q, X, Y, Z, R3, R4, R5, R6, R7, R8, t and R9 are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.
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- 6-(2-Adamantan-2-ylidene-hydroxybenzoxazole)-O-sulfamate: A potent non-steroidal irreversible inhibitor of human steroid sulfatase
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We report the synthesis and results from the in vitro evaluation of 6-(adamantan-2-ylidene-hydroxybenzoxazole)-O-sulfamate 1 as an irreversible inhibitor of human steroid sulfatase (STS). Highly straightforward, condensation of 2-methyl-6-hydroxybenzoxazole with 2-adamantanone, subsequent elimination of water and sulfamoylation provide the title compound in 45% overall yield from the inexpensive 2,4-dihydroxyacetophenone. 1 was found to be a potent irreversible inhibitor of purified human steroid sulfatase (STS) and specific for this enzyme relative to human arylsulfatases A and B. In cellular assays with human keratinocytes, sebocytes and fibroblasts, 1 blocked STS activity with IC50 values in the range of 0.15-0.8 nM, and in MCF-7 breast cancer cells with IC50=2.3 nM, while it did not bind to estrogen receptors α and β. Thus, 1 is a candidate for further investigation of its potential as a drug to be used in androgen- and estrogen-dependent diseases.
- Schreiner, Erwin P.,Wolff, Barbara,Winiski, Anthony P.,Billich, Andreas
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p. 4313 - 4316
(2007/10/03)
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- Compounds enhancing antitumor activity of other cytotoxic agents
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This invention relates to certain heterocyclic compounds and their pharmaceutically acceptable salts, which are useful for sensitizing multidrug-resistant tumor cells to anticancer agents and multidrug resistant forms of malaria, tuberculosis, leishmania and amoebic dysentery to chemotherapeutants. The compounds and their pharmaceutically acceptable salts are also inhibitors of the active drug transport capability of P-glycoprotein which is encoded by the human MDR1 gene, as well as of certain other related ATP-binding-cassette transporters from eukaryotic and prokaryotic organisms (e.g., pfmdr from Plasmodium falciprum, and murine mdr1 and mdr3 gene products).
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- Endothelin receptor antagonists
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Novel compounds of the formula I STR1 in which R 1, R 2, R 3 and X have the meaning indicated in claim 1, and their salts exhibit endothelin receptor-antagonistic properties.
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- Use of zeolite catalysts for efficient synthesis of benzoxazoles via Beckmann rearrangement
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Substituted benzoxazoles have been synthesized in very good yields starting from o-acylphenol oximes via Beckmann rearrangement using zeolite catalysis.
- Bhawal,Mayabhate,Likhite,Deshmukh
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p. 3315 - 3321
(2007/10/03)
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- o-Aminophenol compounds
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o-Aminophenol derivatives are described represented by the formula (I) STR1 wherein R represents --NH2 or --NH--CO--R6 ; R1 and R2 which may be the same or different, each can represent an alkyl group or an aromatic group, or R1 and R2 together can form a ring; or R1, R2 and R3 together can form a ring ; R3 represents hydrogen, an alkyl group or an aromatic group; R4 can represent an alkyl group or an aromatic group; R5 can represent an alkyl group, an alkoxy group, an alkylthio group, an arylthio group, a halogen atom or an acylamino group; and n is 0, 1 or 2; R6 represents an alkyl group or an aromatic group; and R4 and R5 together can form a heterocyclic ring, R1 and R4 together can form a heterocyclic ring, or R1 and R5 together can form a ring; and R1, R2, R3, R4, and R5n have a total of 7 or more carbon atoms.
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