- Synthesis of cyclic D-(+)-camphoric acid imides and study of their antiviral activity
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[Figure not available: see fulltext.] Several D-(+)-camphoric acid imides, not previously described in the literature, were synthesized with good yields. The synthesis of previously known imides was improved. The cytotoxicity and antiviral activity of all synthesized imides were studied.
- Chernyshov, Vladimir V.,Yarovaya, Olga I.,Peshkov, Roman Yu.,Salakhutdinov, Nariman F.
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- Camphor acid acylhydrazone derivative as well as preparation method and application thereof (by machine translation)
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The invention discloses a camphor acid-based acylhydrazone derivative and a preparation method thereof as, well as a preparation method and application of the derivative of the camphor acid-based acylhydrazone derivative (I) as shown: in the following formula (I). The derivative of, R (I) the present, invention is obtained by the, acylation of, camphor acid serving as a raw, 2,3 - material in, 2,6 - the, 2,4 - presence of camphor, 2,5 - acid as a raw material and, 3,4 - then dehydration to, 3,5 - obtain camphor acid, as a, raw material, and then acylation is. carried out with, hydrazine hydrate. NThe novel five-membered, heterocyclic camphor acid-based acylhydrazone derivatives can be used for synthesizing the novel five-membered heterocyclic camphor acid-based acylhydrazone derivatives as a novel; five-membered heterocyclic camphor acid-based acylhydrazone derivative in the catalysis of, an acid catalyst to form a novel five-membered, heterocyclic camphor acid,based acylhydrazone. derivative. (by machine translation)
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Paragraph 0046-0049
(2019/12/31)
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- Composition comprising camphoric acid derivative and application of composition in cosmetics
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The invention provides a composition containing a camphoric acid derivative and application of the composition in cosmetics, and belongs to the technical field of cosmetics. A preparation method of the camphoric acid derivative comprises the following steps: converting camphoric acid into camphoric anhydride, and carrying out N-acylation reaction on the camphoric anhydride and amino acid, and synthesizing to obtain the camphoric acid derivative. The invention also discloses application of the composition containing the camphoric acid derivative in cosmetics. According to the preparation methodof the camphoric acid derivative, the amino acid is introduced into a camphoric acid molecular skeleton, water solubility and cell permeability of camphoric acid can be effectively changed, a novel camphoric acid-based bioactive compound is synthesized, the obtained camphoric acid derivative has a good protection effect on ESF-1 cell senescence caused by UV damage, and skin lesion such as skin thickening and wrinkle generation caused by UV irradiation can be improved.
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Paragraph 0038; 0040; 0044; 0046; 0048; 0050; 0052; 0054; 00
(2019/10/17)
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- BENZAMIDE IMIDAZOPYRAZINE BTK INHIBITORS
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Provided are Bruton's Tyrosine Kinase (Btk) inhibitor compounds according to Formula I, pharmaceutically acceptable salts thereof, pharmaceutical compositions thereof, or their use in therapy.
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Page/Page column 129
(2016/07/27)
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- Modified McFadyen-Stevens reaction for a versatile synthesis of aliphatic/aromatic aldehydes: Design, optimization, and mechanistic investigations
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The traditional McFadyen-Stevens reaction requires harsh alkaline reaction conditions, thus precluding application to the synthesis of aliphatic aldehydes. Our modified McFadyen-Stevens reaction enables the transformation from the N,N-acylsulfonyl hydrazine to the corresponding aldehyde upon treatment with an imidazole-TMS imidazole combination without relying on oxidative or reductive reagents. The reduced basicity and in situ protection of the resulting aldehyde widens the substrate scope to include aliphatic aldehydes, even ones bearing an α-hydrogen atom. Close examination of the side reactions for particular substrates in combination with theoretical considerations via DFT calculations led to a mechanistic understanding of the McFadyen-Stevens reaction involving an acyl diazene and a hydroxy carbene as reasonable intermediates.
- Iwai, Yuri,Ozaki, Takashi,Takita, Ryo,Uchiyama, Masanobu,Shimokawa, Jun,Fukuyama, Tohru
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p. 1111 - 1119
(2013/06/04)
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- Total synthesis of a possible specific and effective acid-targeted cancer diagnostic, a camphor derived bis-N-oxide dimer
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Possible specific and effective acid-targeted cancer diagnostics and therapeutics, a camphor derived bis-N-oxide dimer was synthesized in 12-steps from commercially available (+)-camphoric acid and seven-steps from a common intermediate, a camphor derived primary amine.
- Boeckman Jr., Robert K.,Miller, Yan,Savage, Dennis,Summerton, James E.
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scheme or table
p. 2243 - 2245
(2011/05/05)
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- Synthesis of d-camphor based γ-amino acid (1S,3R)-3-amino-2,2,3-trimethylcyclopentane carboxylic acid
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Synthesis of a γ-amino acid derived from (1R,3S)-camphoric acid is described. d-(+)-Camphoric anhydride, prepared from d-(+)-camphoric acid by treatment with methanesulfonyl chloride and triethylamine, was reacted with benzyl alcohol and catalytic DMAP, and subsequently reacted in a Curtius rearrangement to afford the corresponding carbamate derivative. This derivative was converted to the desired γ-amino acid through hydrogenolysis.
- Eagles, Joel B.,Hitchcock, Shawn R.
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experimental part
p. 519 - 523
(2010/07/20)
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- Activation of molecular oxygen and its use in stereoselective tetrahydrofuran-syntheses from δ,ε-unsaturated alcohols
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Bishomoallylic alcohols (pent-4-en-1-ols) underwent efficient oxidative cyclizations, if treated with O2 and bis{2,2,2-trifluoromethyl-1- [(1R,4S)-1,7,7-trimethyl-2-(oxo-κO)bicyclo[2.2.1]hept-3-yliden] ethanolato-κO}cobalt(ii) in solutions of 2-propanol at 60 °C. Ring closures occurred diastereoselectively and afforded 2,3-trans- (96% de), 2,4-cis- (～60% de), and 2,5-trans-substituted (>99% de) (phenyl)tetrahydrofur-2-ylmethanols as major components. Formation of bicyclic compounds and a 2,3,4,5-substituted oxolane was feasible as exemplified by syntheses of oxabicyclo[4.3.0]nonylmethanols and a derivative of natural product magnosalicin in 61-72% (90-99% de). The effectiveness of tetrahydrofuran synthesis was critically dependent on (i) solvent, (ii) reaction temperature, (iii) initial cobalt concentration, (iv) chain length between hydroxyl and vinyl groups, and (v) substitution at reacting entities. A sequence is proposed for rationalizing observed selectivities.
- Menendez Perez, Barbara,Schuch, Dominik,Hartung, Jens
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supporting information; experimental part
p. 3532 - 3541
(2009/02/05)
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- Synthesis of 1,11,11-trimethyl-3,6-diazotricyclo [6.2.1.0 2,7]undeca-2,6-diene and 1,15,15-trimethyl-3,10-diazotetracyclo[10.2. 1.02,11.04,9]pentadeca-2,4(9),5,7,10-pentaene from camphoroquinone enantiomers
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Optically active camphordihydro-2,3-pyrazine and camphorquinoxaline were prepared from camphoroquinone enantiomers. It was shown that (1S,4R)-(+)-camphoroquinone was formed by oxidation of (1S,3R, 4R)-(-)-3-bromocamphor and (1R,4S)-(-)-camphoroquinone from (1R,3S, 4S)-(+)-3-bromocamphor, respectively. Camphor anhydride was a side product (6-10%) of the reaction. Springer Science+Business Media, Inc. 2007.
- Adamenko,Frolova,Panteleeva,Kuchin
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- Synthesis of camphoric anhydride via unsensitized photo-oxidation of camphorquinone
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Camphorquinone undergoes a novel unsensitized photo oxidation in polar solvents such as alcohol under oxygen to give camphoric anhydride in 85% yield irradiated with a high-pressure mercury lamp. A possible mechanism is also presented in terms of results of experiment.
- Ji, Shun-Jun,Lu, Jianmei,Lang, Jian-Ping,Horiuchi, C. Akira
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p. 1659 - 1663
(2007/10/03)
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- Synthesis of (3S,4R)-(+)-hydroxymethyl-3-(trifluoromethyl)-4,5,5-trimethylcyclopentene - a trifluoromethyl analogue of necrodols
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New trifluoromethyl group containing enantiomerically pure monoterpene derivatives, methyl (1S,3R,4S)-(+)-4-(trifluoromethyl)-2,2,3-trimethylcyclopentanecarboxylate (6); methyl (3S,4R)-(+)-3-(trifluoromethyl)-4,5,5-trimethylcyclopentenecarboxylate (10) and (3S,4R)-(+)-hydroxymethyl-3-(trifluoromethyl)-4,5,5-trimethylcyclopentene (1), were prepared using camphoric anhydride as the starting material and sulphur tetrafluoride as the fluorinating agent. Compound 1 is a trifluoromethyl analogue of an unknown isomer of necrodols.
- Dmowski, Wojciech,Piasecka-Maciejewska, Krystyna
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- Selective fluorination of (1R,3S)-(+)-camphoric acid with sulphur tetrafluoride. Preparation of fluorinated optically active derivatives of 1,2,2-trimethylcyclopentane
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Treatment of (1R,3S)-(+)-camphoric acid (1) with sulphur tetrafluoride at ambient temperature gives, in general, three products: 1,2,2-trimethyl-3-trifluoromethyl-1-cyclopentanoyl fluoride (2), 2,2,4,4-tetrafluoro-1,8,8-trimethyl-3-oxa-bicyclo[3.2.1]octane (3) and camphoroyl difluoride (4). The ratio of products strongly depends on the reaction time. Alkaline hydrolysis of (2) gives 1,2,2-trimethyl-3-trifluoromethyl-1-cyclopentanecarboxylic acid (5), quantitatively. All products exhibit optical activity.
- Dmowski, Wojciech,Kozlowski, Tomasz
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p. 187 - 190
(2007/10/03)
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- Chiral carboxylic acid ligands derived from camphoric acid
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Versatile and convenient preparations of chiral carboxylic acid ligands, derived from camphoric acid, are described, either by esterification of camphoric dichloride or by a regioselective opening of the corresponding anhydride by a variety of alcohols or diols.
- Moloney, Mark G.,Paul, Diana R.,Thompson, Russell M.,Wright, Emma
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p. 2551 - 2562
(2007/10/03)
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- Photoinduced Molecular Transformations. Part 106. The Formation of Cyclic Anhydrides via Regioselective β-Scission of Alkoxyl Radicals generated from 5- and 6-Membered α-Hydroxy Cyclic Ketones.
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The irradiation of the hypoiodites of 5- or 6-membered cyclic α-ketols in benzene containing mercury(II) oxide and iodine (each 3 equiv.) resulted in the formation of the corresponding cyclic anhydrides arising from the insertion of an oxygen.A novel formation of a methylenedioxy group arising from an intramolecular hydrogen abstraction, on the other hand, was found when a steroidal α,α-dimethoxy alcohol hypoiodite was irradiated in benzene.An 18O labelling study of the formation of the cyclic anhydride on photolysis of 17β-hydroxy-4β-methoxy-5α-androstan-16-one hypoiodite generated in situ by an excess of mercury(II) oxide and iodine in benzene indicated that the heavy oxygen of Hg18O is incorporated as the ring oxygen of the anhydride.On the basis of this result, a pathway involving a regioselective β-scission of the alkoxyl radical is proposed as leading to formation of the cyclic anhydride.
- Suginome, Hiroshi,Satoh, Gen,Wang, Jian Bo,Yamada, Shinji,Kobayashi, Kazuhiro
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p. 1239 - 1245
(2007/10/02)
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- Defense Mechanisms of Arthropods. 84. Synthesis of (-)-α-Necrodol and (-)-β-Necrodol: Novel Cyclopentanoid Terpenes from a Carrion Beetle
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Syntheses of (-)-α-necrodol (1) and (-)-β-necrodol (2) from (+)-phenylcamphoric acid (7a) are described.In addition, several related compounds, (+)-epi-α-necxrodol (3), (+)-epi-β-necrodol (4), and (+)-γ-necrodol (5), have been prepared.The absolute configuration of natural α-necrodol has been established as 3R,5R by comparison of its (+)-α-methoxy-α-(trifluoromethyl)phenylacetyl ester with the ester derived from synthetic 1.
- Jacobs, Robert T.,Feutrill, Geoffrey I.,Meinwald, Jerrold
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p. 4051 - 4062
(2007/10/02)
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- PHOTOSENSITIZED OXYGENATION OF 3-DIAZOCAMPHOR
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Photosensitized oxygenation of 3-diazocamphor gave camphorquinone and camphoric anhydride in benzene.The yield of camphoric anhydride did not depend on the concentration of added camphorquinone or of diazocamphor.When the reaction was carried out in acetonitrile or benzonitrile, amide 7 or 8 was produced.The formation of amide strongly supports the intermediacy of carbonyl oxide.
- Okada, Keiji,Mukai, Toshio
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p. 359 - 360
(2007/10/02)
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