- Asymmetric synthesis of an axially chiral antimitotic biaryl via an atropo-enantioselective Suzuki cross-coupling
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A catalytic asymmetric synthesis of the axially chiral bridged biaryl (-)-2, a structural analogue of natural (-)-rhazinilam possessing original antimitotic properties, is described. The key step is an intermolecular asymmetric Suzuki coupling, furnishing the nonbridged biaryl (-)-6, precursor of (-)-2, with up to 40% ee using binaphthyl ligand 7a. Various known or new binaphthyl and ferrocenyl phosphines as well as phosphetanes were screened as ligands in this reaction, the conditions of which were optimized. The comparison with another Suzuki coupling system showed that 7a is the most versatile ligand described to date for this type of transformation. This work gives the first application of the asymmetric Suzuki coupling to a biologically relevant target.
- Herrbach, Audrey,Marinetti, Angela,Baudoin, Olivier,Guenard, Daniel,Gueritte, Francoise
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Read Online
- A compound with anti-tumor activity of the multitarget kinase inhibitor and its preparation method
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The invention relates to the technical field of medicine, and relates to a type of compounds with antitumor activities, and a preparation method and an application thereof. The compounds have a structural general formula represented below. R1 is alkyl group, heterocyclic group, substituted phenyl group, substituted alicyclic group, or aliphatic heterocyclic group, wherein the substituent is 2,3-ethylenedioxy, 3,4-ethylenedioxy, 2,3-methylenedioxy, or 3,4-methylenedioxy; or all-site-substituted hydrogen, alkyl, alkoxy, halogen, amino, hydroxyl, trifluoromethyl, formate, and the like. R2 is heterocyclic group or substituted phenyl group, wherein the phenyl substituent is 2,3-ethylenedioxy, 3,4-ethylenedioxy, 2,3-methylenedioxy, or 3,4-methylenedioxy; or all-site-substituted hydrogen, alkyl, alkoxy, halogen, amino, hydroxyl, trifluoromethyl, formate, and the like. The compounds provided by the invention have substantial tumor cytotoxic effect and broad-spectrum kinase inhibitory activity, and can be used in preparing antitumor medicines.
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- Indole and quinoline derivatives and its preparation method and application
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The invention provides an indoloquinoline derivative, a preparation method and application thereof in preparing antitumor drugs and antiviral drugs. The chemical structure of the indoloquinoline derivative is shown as a formula I. Experiments show that a partly-boric-acid-modified indoloquinoline derivative and a non-boric-acid-modified indoloquinoline derivative have strong inhibition effect on various tumor cell strains, thereby being capable of being used for preparation of the antitumor drugs, and have strong antiviral activity, thereby being capable of being used for preparation of the antiviral drugs.
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Paragraph 0183; 0184
(2017/02/28)
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- Process for the preparation of aminoaryl- and aminoheteroaryl boronic acids and esters
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The present invention relates to a process for the preparation of aminoaryl- and aminoheteroaryl boronic acids and esters of formula (I) in high yields The claimed process uses diarylketal formula (V) to generate an arylbromid of formula (III) in which the amino-group is protected as bisarylmethylidenimino-group:
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Paragraph 0053; 0056; 0058
(2014/11/27)
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- PROCESS FOR THE PREPARATION OF AMINOARYL- AND AMINOHETEROARYL BORONIC ACIDS AND ESTERS
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The present invention relates to a process for the preparation of aminoaryl- and aminoheteroaryl boronic acids and esters thereof of formula (I) in high yield. The claimed process uses diarylketal formula (V) to generate an arylbromide of formula (III) in which the amino-group is protected as bisarylmethylidenimino-group, which is then transformed into a formula (I) compound.
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Page/Page column 15; 16; 17; 18
(2014/12/09)
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- Novel inhibitors of bacterial biofilms and related methods
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Multi-cyclic compounds of chemical structure represented by formula given below and compositions thereof are useful for reducing or inhibiting the growth of bacterial biofilms and for controlling bacterial biofilm infections. Such compounds and compositions are also useful in methods for reducing or inhibiting the growth of biofilms and for controlling bacterial biofilm infections involving biofilms.
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Paragraph 0184-0185
(2014/05/06)
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- Inhibitors of bacterial biofilms and related methods
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Certain multi-cyclic compounds and compositions thereof are useful for reducing or inhibiting the growth of bacterial biofilms and for controlling bacterial biofilm infections. Such compounds and compositions are also useful in methods for reducing or inhibiting the growth of biofilms and for controlling bacterial biofilm infections involving biofilms.
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Page/Page column 116
(2012/12/13)
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- 1,3,5-Tris(2′-aminophenyl)benzene: A novel platform for molecular receptors
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The synthesis of a novel, rigid, aromatic platform for molecular receptors is described. 1,3,5-Tris(2′-aminophenyl)benzene was prepared via Suzuki-Miyaura cross-coupling reactions of 2-aminophenylboronic acid with 1,3,5-triiodobenzene in the presence of Ba(OH)2, Pd(OAc)2 and (2-biphenyl)dicyclohexylphosphine. Alternatively, one-pot borylation of 2-bromoaniline and cross-coupling of the resulting boronate ester with 1,3,5-triiodobenzene was investigated. Georg Thieme Verlag Stuttgart.
- Pia?tek, Piotr,S?omiany, Norbert
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p. 2027 - 2030
(2008/02/05)
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- Fused heterotricyclic compounds as inhibitors of 17beta-hydroxysteroid dehydrogenase 3
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Fused heterotricyclic compounds, methods of using such compounds in the treatment of hormone sensitive diseases such as prostate cancer, and pharmaceutical compositions containing such compounds.
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Page/Page column 47
(2008/06/13)
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- Process for the preparation of aniline boronic acids and derivatives thereof
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Production of anilineboronic acid derivatives (I) comprises converting an aniline compound (II) to a doubly protected derivative (III), metallating (III) and simultaneously or subsequently reacting it with a borate ester (IV) to give a protected anilineboronic acid ester (V), and deprotecting (V). Production of anilineboronic acid derivatives of formula (I) comprises converting an aniline compound of formula (II) to a doubly protected derivative of formula (III), metallating (III) and simultaneously or subsequently reacting it with a borate ester of formula (IV) to give a protected anilineboronic acid ester of formula (V), and deprotecting (V): [Image] PG : protecting group; R : H, halo, 1-20C alkyl or alkoxy, optionally substituted 6-12C aryl or aryloxy, heteroaryl or heteroaryloxy, optionally substituted 3-8C cycloalkyl, dialkylamino, diarylamino, alkylthio, arylthio, ester or acetal; X : H or halo; R1>-R3>H or optionally substituted 1-20C alkyl, or two of R1>-R3> can form a ring or another borate group.
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- DIARYLUREA DERIVATIVES AND THEIR USE AS CHLORIDE CHANNEL BLOCKERS
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The present invention relates to novel diarylurea derivatives useful as chloride channel blockers. In other aspects the invention relates to the use of these compounds in a method for therapy, such as for the treatment of bone metabolic diseases, diseases responsive to modulation of the mast cell or basophil activity, diseases responsive to inhibition of angiogenesis, or sickle cell anaemia, and to pharmaceutical compositions comprising the compounds of the invention.
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- Design of chiral boronate-substituted acrylanilides. Self-activation and boron-transmitted 1,8-stereoinduction in [4+2] cycloaddition
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The [4+2] cycloaddition of ortho-boronoanilide dienophile 4 with cyclopentadiene was found to proceed faster than both its para isomer 8 and the unsubstituted derivative 6, thereby confirming that self-activation by internal coordination is operative in the case of 4. Chiral boronic esters derivatives 9-13 provided a small level of remote 1,8-stereoinduction transmitted through a putative tetrahedral stereogenic boronate complex. These results show that dialkoxyboronic esters can operate as weak, internal Lewis acids and activate carbonyl-containing functionalities in cycloaddition reactions.
- Kennedy, Jason W.J.,Hall, Dennis G.
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p. 263 - 270
(2007/10/03)
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- Self-activation and 1,8-stereoinduction in a boronate-substituted dienophile
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The [4+2] cycloaddition of ortho-boronoanilide dienophile 4 with cyclopentadiene was found to proceed faster than both its para isomer 8 and the unsubstituted derivative 6, thereby confirming that self-activation by internal coordination is operative in the case of 4. Chiral boronic esters derivatives 9 and 10 provided a small level of remote 1,8-stereoinduction. These results show that dialkoxyboronic esters can operate as weak, internal Lewis acids and activate carbonyl-containing functionalities in cycloaddition reactions.
- Kennedy, Jason W. J.,Hall, Dennis G.
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p. 477 - 479
(2007/10/03)
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- Boron heterocycles bearing a peripheral resemblance to naturally-occurring purines: Design, syntheses, structures and properties
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To test the design and initiate the development of a new class of boron-containing purine nucleoside and aglycon analogs, the benzo-fused boron heterocycles 1-hydroxy-1H-2,4,1-benzoxazaborine (2), 1,2-dihydro-1-hydroxy-2,4,1-benzodiazaborine (3), and 3-amino-1,2-dihydro-1-hydroxy-2,4,1-benzodiazaborine (4) were synthesized, and their structural properties and chemical reactivities were investigated. The heterocyclic peripheries of these targets possess heteroatom, hydrogen atom, and in-plane lone-pair electron loci specifically selected to match closely those of the pyrimidine ring portions of the naturally-occurring purines adenine, hypoxanthine, and guanine. According to 1H and 11B NMR spectral analyses, 2-4 are stable to facile hydrolysis, but not to facile hydration, which occurs in a 1,4-fashion to give zwitterionic adducts. In addition, these benzo-fused boron heterocycles form bis-methanol adducts simply upon warming in methanol solution. A single-crystal X-ray diffraction analysis of the bis-methanol adduct (14) derived from 3 confirmed it to be a zwitterion comprised of tetrahedral borate anion and formamidinium cation molecular fragments. From NMR-based solution structure determinations made of 2-4 and a series of substituted derivatives, the facile 1,4-hydration property appears to be endemic to the 2,4,1-oxaza- and diazaborine classes of boron heterocycles and is projected to imbue certain future imidazo[5,4-e]-fused members with the requisite aqueous solution structural features for 'transition-state' analog inhibition of the enzyme adenosine deaminase (EC 3.5.4.4). This work underscores the attraction of employing boron-for-carbon replacement strategies in the design of new, potentially bioactive agents.
- Groziak,Ganguly,Robinson
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p. 7597 - 7605
(2007/10/02)
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