- Solanesol derived therapeutic carriers for anticancer drug delivery
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Metabolites of a large number of inert drug carriers can cause long-term exogenous biological toxicity. Therefore, carriers with simultaneous therapeutic effects may be a good choice for drug delivery. Herein, a series of pharmacologically active solaneso
- Xiong, Yao,Hou, Tian,Liu, Lei,Peng, Wanjia,Wang, Chunyun,Lu, Yan,Wang, Shuaichao,Shi, Jiahua,Song, Shiyong
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- Synthesis of solanesyl phosphonate
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Three solanesyl phosphonates were synthesized using standard Arbuzov reaction, and their structures were determined by ESI-MS, NMR, and IR. Copyright Taylor & Francis Group, LLC.
- Lingbo, Qu,Xiaona, Shi,Xiaolan, Chen,Libo, Fan
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- Synthesis of [3′-14C] coenzyme Q10
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Radio-labelled coenzyme Q10, labelled at the 3′-position with 14C, was synthesized starting from natural solanesol and ethyl [3-14C] acetoacetate. The radiochemical yield was 8.0% from ethyl [3-14C] acetoacetate
- Hamamura, Kimio,Yamatsu, Isao,Minami, Norio,Yamagishi, Yoji,Inai, Yuichi,Kijima, Shizumasa,Nakamura, Tetsuya
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- A solanesol-derived scaffold for multimerization of bioactive peptides
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A flexible molecular scaffold bearing varying numbers of terminal alkyne groups was synthesized in five steps from solanesol. R(CO)-MSH(4)-NH2 ligands, which have a relatively low affinity for binding at the human melanocortin 4 receptor (hMC4R), were prepared by solid phase synthesis and were N-terminally acylated with 6-azidohexanoic acid. Multiple copies of the azide N3(CH2)5(CO)-MSH(4)-NH2 were attached to the alkyne-bearing, solanesol-derived molecular scaffold via the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. Control studies showed that the binding affinity of the triazole-containing ligand, CH 3(CH2)3(C2N3)(CH 2)5(CO)-MSH(4)-NH2, was not significantly diminished relative to the corresponding parental ligand, CH3(CO)- MSH(4)-NH2. In a competitive binding assay with a Eu-labeled probe based on the superpotent ligand NDP-α-MSH, the monovalent and multivalent constructs appear to bind to hMC4R as monovalent species. In a similar assay with a Eu-labeled probe based on MSH(4), modest increases in binding potency with increased MSH(4) content per scaffold were observed.
- Alleti, Ramesh,Rao, Venkataramanarao,Xu, Liping,Gillies, Robert J.,Mash, Eugene A.
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- Synergistic factors ensue high expediency in the synthesis of menaquinone [K2] analogue MK-6: Application to access an efficient one-pot protocol to MK-9
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Here we report a practical and efficient method for the synthesis of menaquinone vitamin (K2) analog MK-6 in all trans forms through “1 + 5 convergent synthetic approach” of pentaprenyl chloride with monoprenyl menadione derivative. In the synergistic factors, less efficient leaving group/more efficient nucleophile (Cl) in the substrate makes it more prominent reaction by eliminating all Sn2’ side reaction products. Further, the addition of acetic acid in the last step (desulfonation) of reaction sequence removes the limitations of the reactions in terms of cyclized side product (multiple reactions of pentaprenyl alcohol with Et3B), byproduct (Et3B, incendiary compound) formations and their interruption in the tricky purification processes. The utility of this method was further extended to find an efficient one-pot synthesis to MK-9 to the gram scale synthesis. This approach is economical and efficient and avoids the awkward chromatographic separation processes.
- Yerramsetti, Nanaji,Dampanaboina, Lavanya,Mendu, Venugopal,Battula, Satyanarayana
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- New efficient synthesis of ubiquinones
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A strategy for the ecofriendly and high-yielding synthesis of ubiquinones starting from simple materials and using mild conditions is reported. CoQ1, CoQ2, CoQ3, and CoQ9 were prepared. Copyright Taylor & Francis Group, LLC.
- Bovicelli, Paolo,Borioni, Giorgio,Fabbrini, Danilo,Barontini, Maurizio
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p. 391 - 400
(2008/04/01)
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- Novel Intermediates, Process for Their Preparation and Process for the Preparation of Coq10 Employing the Said Novel Intermediates
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The present invention relates to an improved process for the preparation of Coenzyme Q. Coenzyme Q10 or CoQ10 has the chemical name 2-[(all-trans)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl]-5,6-dimethoxy-3-methyl-1,4-benzoquinone and has the formula I. The invention also provides new intermediates useful for the preparation of CoQ10 and processes for their preparation.
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Page/Page column 16
(2008/12/08)
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- IMPROVED PROCESSES FOR THE PREPARATION OF PURIFIED SOLANESOL, SOLANESYL BROMIDE AND SOLANESYL ACETONE
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The present invention relates to processes for the prepartion of purified solanesol, solanesyl bromide and solanesyl acetone. Solanesyl acetone has the chemical name - all - trans 6, 10, 14, 18, 22, 26, 30, 34, 38 -nonamethyl -5,9, 13, 17, 21, 25, 29, 33, 37- triacontanonaen-2-one, of formula (I) and is used for synthesis of coenzyne Q10.
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Page/Page column 16; 17
(2008/06/13)
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- Synthetic studies on coenzyme Q10: Part 31) - An improved C5 + C45 approach to the stereoselective synthesis of coenzyme Q10 via metal-halogen exchange strategy
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An efficient and stereoselective approach to the synthesis of coenzyme Q10 is described (Scheme). The MeOCH2-protected p-hydroquinone 4 containing the C5 (E)-allyl (tert-butyl) dimethylsilyl ether moiety was obtained via a halogen-lithium exchange of the MeOCH2-proctected 2-bromo-5,6-dimethoxy-3-methylhydroquinone 2 and subsequent addition to (E)-(tBuMe2Si)-OCH 2C(Me)= CHCH2Br (3). The reductive desulfonylation of compound 8, obtained from 4 via 5-7, was successfully carried out by employing Li/EtNH2.
- Yu, Xiong-Jie,Dai, Hui-Fang,Chen, Fen-Er
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p. 967 - 971
(2008/02/04)
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- Radical-scavenging polyphenols: New strategies for their synthesis
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New strategies for the synthesis of polyphenols, compounds with antioxidant properties contained in every kind of plants, are discussed. Syntheses of different classes of polyphenols, namely ubiquinones, present in many natural systems in which electron-transfer mechanisms are involved, hydroxytyrosol, one of the main components of the phenol fraction in olives, and flavonoids, widespread in the plant kingdom, were approached by simple and environmentally sustainable methods.
- Bovicelli, Paolo
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p. 1703 - 1710
(2008/03/11)
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- The Friedel-Crafts allylation of a prenyl group stabilized by a sulfone moiety: Expeditious syntheses of ubiquinones and menaquinones
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An efficient synthetic method for the protected p-hydroquinone compounds 4 containing the C5 trans allylic sulfone moiety has been developed by the direct Friedel-Crafts allylation of the protected dihydroquinone 2 with 4-chloro-2-methyl-1-phenylsulfonyl-2-butene (7a) or 4-hydroxy-2-methyl-1-phenylsulfonyl-2-butene (7b). Expeditious total syntheses of coenzyme Q-10 and vitamin K2(20) have been demonstrated from these valuable key compounds 4a and 4b.
- Min, Jae-Hong,Lee, Jun-Sup,Yang, Jae-Deuk,Koo, Sangho
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p. 7925 - 7927
(2007/10/03)
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- Synthesis and spectroscopic characterization of 1-13C- and 4-13C-plastoquinone-9
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This paper presents the synthesis of 1-13C- and 4-13C-plastoquinone-9 and their characterization with NMR spectroscopy and mass spectrometry. The synthetic scheme has been further adapted to introduce 13C-labeled plastoquinones on all individual and on each combination of positions in the quinone ring. Also a two-step scheme is disclosed to prepare unlabeled plastoquinone-9. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
- Boers, Rutger B.,Randulfe, Yolanda Pazos,Van Der Haas, Hendrikus N. S.,Van Rossum-Baan, Marleen,Lugtenburg, Johan
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p. 2094 - 2108
(2007/10/03)
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- Synthesis and spectroscopic characterisation of 13C-labelled ubiquinone-0 and ubiquinone-10
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(1-13C)-, (2-13C)-, (3-13C)-, (3-13CH3)-, (4-13C)-, and (13CH3O)2-ubiquinone-10 and the corresponding (1-13C)-, (6-13C)-, (5-13C)-, (5-13CH3)-, (4-13C)-, and (13CH3O)2-ubiquinone-0 have been synthesised from simple labelled starting materials via a single reaction scheme.The ubiquinones have been characterised using mass spectrometry, 1H NMR and 13C NMR.The spectroscopic results indicate that, within experimental error, the syntheses have been accomplished without scrambling or dilution of label.All labelled ubiquinones have been synthesised on a decigram scale.
- Liemt, W. B. S. van,Steggerda, W. F.,Esmeijer, R.,Lugtenburg, J.
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p. 153 - 162
(2007/10/02)
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- SYNTHESIS OF all-(E)-DECAPRENOL AND ITS 2Z ISOMER
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C5-chain growth in the structure of natural solanesol, isolated from tobacco, was realized by a C3 + C2 scheme.Decaprenol was separated into isomers with respect to the newly formed double bond by column chromatography on silica gel.The isomeric compositi
- Kozlova, I. V.,Obol'nikova, E. A.,Kogan, L. M.,Filippova, T. M.,Kharchevnikov, A. P.,Samokhvalov, G. I.
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p. 1055 - 1061
(2007/10/02)
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- Synthetic Studies on Isoprenoidquinones. II. Syntheses of Ubiquinone-10, Phylloquinone, and Menaquinone-4 by a Chain-Extending Method Utilizing Terminally Functionalized Isoprenoidhydroquinones
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Physiologically active polyisopreoidquinones, ubiquinone-10 (coenzyme Q10), phylloquinone (vitamin K1), and menaquinone-4 (vitamin K2(20)) were synthesized by a chain-extending method utilizing protected hydroquinones with the omega-hydroxyprenyl or omega-hydroxygeranyl side chain.Conditions for reductive desulfurization subsequent to allylic homologation was investigated. Keywords - polyisoprenoidquinone synthesis; ubiquinone-10; phylloquinone; menaquinone-4; chain-extending method; sulfone coupling; reductive desulfurization
- Masaki, Yukio,Hashimoto, Kinji,Kaji, Kenji
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p. 3959 - 3967
(2007/10/02)
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- REGIOSELECTIVE POLYPRENYL REARRANGEMENT OF POLYPRENYL 2,3,4,5-TETRASUBSTITUTED PHENYL ETHERS PROMOTED BY BORON TRIFLUORIDE
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4-Acetoxy-6-polyprenyl-2,3,5-trimethylphenols or 2,3-dimethoxy-5-methyl-6-polyprenylhydroquinones were obtained selectively by the BF3*OEt2 catalyzed polyprenyl rearrangement of polyprenyl 4-acetoxy-2,3,5-trimethylphenyl ethers or polyprenyl 2,3-dimethoxy-4-hydroxy-5-methylphenyl ethers.
- Yoshizawa, Toyokichi,Toyofuku, Hatsunori,Tachibana, Koichi,Kuroda, Toshio
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p. 1131 - 1134
(2007/10/02)
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