- myo-inositol 4,6-carbonate: An easily prepared small molecule with three syn-axial hydroxyl groups
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myo-Inositol 4,6-carbonate, a compound having three syn-axial hydroxyl groups, was synthesized in four steps suitable for gram-scale preparation. It readily forms complexes with cations.
- Angyal
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- Formation of (±)-1,2-O-ethylidene-myo-inositol during the reaction between triethyl orthoformate and myo-inositol in DMSO
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Besides myo-inositol monoorthoformate (1), (±)-1,2-O-ethylidene-myo-inositol (2) was obtained as another product in the reaction between triethyl orthoformate and myo-inositol in DMSO catalyzed by acid under N2.
- Zhu,Li
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- First synthesis of 3-O-methyl-scyllo-inosamine, a natural product which favors the Rhizobium-Leguminosae symbiosis
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Rhizopine, extracted in small amounts from nodules induced by Sinorhizobium meliloti strain L5-30 infection of alfalfa, was proved to possess the 3-O-methyl-scyllo-inosamine gross structure.
- Krief, Alain,Dumont, Willy,Billen, Denis,Letesson, Jean-Jacques,Lestrate, Pascal,Murphy, Peter J.,Lacroix, Damien
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- Silver (I) oxide assisted O-alkylation of 2,4-di-O-benzoyl-myo-inositol-1,3,5-orthoformate and its 6-O-substituted derivatives: Transannular participation of oxygen
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The reaction of 2,4-di-O-benzoyl-myo-inositol-1,3,5-orthoformate and its 6-O-substituted derivatives with alkyl halides in the presence of silver (I) oxide has been studied systematically. The nature of the product obtained depends on the amount of silver (I) oxide and alkyl halides used as well as on the solvent employed for the reaction. By varying these parameters, the corresponding symmetrical 4,6-di-O-alkylated or 4-mono-O-alkylated myo-inositol-1,3,5-orthoformates can be obtained in good yields. These alkylations proceed by two different pathways which involve the transannular participation of the neighbouring oxygen. Results presented for the allylation of 2,4-di-O-benzoyl-myo-inositol-1,3,5-orthoformate suggest cleavage and allylation of the axial 4-benzoate moiety prior to allylation of the free C-6-hydroxyl group. Involvement of a myo-inositol orthoformate-silver complex during these alkylation reactions is suggested.
- Das, Tanya,Shashidhar
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- 2-O-Benzoyl-myo-inositol-1,3,5-orthoformate
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Protected myo-inositol derivatives are important precursors in the synthesis of phosphorylated myo-inositol derivatives, which play a significant role in cellular signal transduction. The structure of the title compound, C14H14O
- Samanta, Uttamkumar,Puranik, Vedavati G.,Chakrabarti, Pinak,Thoniyot, Praveen,Shashidhar, Mysore S.
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- Exciplex and excimer molecular probes: Detection of conformational flip in a myo-inositol chair
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2-O-tert-Butyldimethylsilyl-4,6-bis-O-pyrenoyl-myo-inositol-1,3, 5-orthoformate (6) and 2-O-tert-butyldimethylsilyl-4-O-[4-(dimethylamino) benzoyl]-6-O-pyrenoyl-myo-inositol-1,3,5-orthoacetate (10) adopt conformationally restricted unstable chairs with fi
- Kadirvel, Manikandan,Arsic, Biljana,Freeman, Sally,Bichenkova, Elena V.
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- ACETYLATED PRODRUGS FOR DELIVERY ACROSS THE BLOOD-BRAIN BARRIER
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The present disclosure relates to pharmaceutical compositions including a compound derived from a parent compound having a hydroxyl or amino moiety, wherein the hydroxyl in the parent compound is presented as an ester in the compound or the amino in the parent compound is presented as an amide in the compound, and their use to prevent or treat neurological disease.
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Page/Page column 32 - 34
(2019/11/12)
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- Lithium hydride as an efficient reagent for the preparation of 1,2-anhydro inositols: Does the reaction proceed through ‘axial rich’ conformation?
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scyllo-Inositol derived 1,2-trans-diequatorial halohydrins can be efficiently converted to the corresponding epoxides in the presence of lithium hydride. The structure of one of the epoxides was determined by single crystal X-ray diffraction analysis. Thi
- Sarkar, Nitai,Sardessai, Richa S.,Shashidhar, Mysore S.,Tamboli, Majid I.,Gonnade, Rajesh G.
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- 4,6-DI-(O-THIOPHOSPHATE)-INOSITOL-1,2,3,5-TETRA-O-SULFATE FOR C. DIFFICILE INFECTION
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The present invention relates to inositol bisthiophosphates-tetrakissulfates, particularly for use in treating symptoms associated with Clostridium difficile infection.
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Page/Page column 4
(2017/07/23)
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- INOSITOL DERIVATIVES FOR USE IN PATHOLOGICAL CRYSTALLIZATION
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The present invention relates to inositol derivatives covalently modified with one, two or three solubility functions, particularly polyethylene glycol moieties, for use in therapy or prevention of conditions related to pathological calcium crystallizatio
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Page/Page column 23
(2017/07/06)
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- Phosphoric acid phaseomannite class compound and its preparation method and application (by machine translation)
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The invention discloses a phaseomannite class phosphate compound, phosphoric acid phaseomannite class compound preparation method, and these phosphoric acid phaseomannite class compounds in the preparation of an anti-tumor drug. The use of non-small cell lung cancer cells to the compounds of this invention to inhibit the growth of tumor cells in active testing, that the compounds of this invention have high inhibition of tumor cell growth activity, some of the compound inhibiting activity even with cisplatin active quite, which indicates that the compounds of this invention have good cell penetrability and phosphorus esterase stability, can be used for the development of anti-tumor medicament. (by machine translation)
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Paragraph 0355-0357; 0358
(2017/07/14)
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- Synthesis and screening of novel inositol phosphonate derivatives for anticancer functions in vitro
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Phosphonates have been frequently used as suitable isosteric and isoelectronic replacements for biologically important phosphates in the development of drugs or drug candidates because of their stability toward the action of phosphatases and other enzymes. In this paper, 12 mono-phosphonate inositol compounds were prepared with phosphonate instead of phosphate by two kinds of strategies, nucleophilic substitution and Arbuzov rearrangement, respectively. All compounds were evaluated in vitro for their activity against non-small cell lung cancer (NSCLC) cell line A549. Two compounds (3ac and 3bb) exhibited good antitumor activity at 10 μg/mL.
- Chen, Wen-Bin,Liu, Jian-Bing,Dou, Dao-Lei,Song, Fan-Bo,Li, Lu-Yuan,Xi, Zhen
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p. 329 - 333
(2015/04/14)
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- Desymmetrization of 4,6-diprotected myo-inositol
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The asymmetric desymmetrization of 4,6-diprotected myo-inositol derivatives was achieved by using a bifunctional, readily available nucleophilic catalyst. The orthogonally protected products were obtained in 80-99% yield with 90-99% ee. Such structures serve as potential enantiopure building blocks for the synthesis of myo-inositol phosphates.
- Lauber, Markus B.,Daniliuc, Constantin-Gabriel,Paradies, Jan
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p. 7409 - 7411
(2013/09/23)
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- H2SO4-silica: An eco-friendly heterogeneous catalyst for the differential protection of myo-inositol hydroxyl groups
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There is enormous interest in myo-inositol derivatives as they serve as precursors for the synthesis of several biologically important phosphoinositols, natural products, catalyst, supramolecular architectures etc. However the presence of six secondary hy
- Vibhute, Amol M.,Sureshan, Kana M.
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p. 7321 - 7329
(2013/07/05)
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- Synthesis and antitumor activity of inositol phosphotriester analogues
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Inositol phosphates, as important second messengers of signal transduction, regulate many biological functions. However, cell penetration and phospholipase stability could be two main issues faced by inositol phosphate analogues used as lead compounds for drug discovery. Inositol phosphotriester analogues could be more beneficial to diffuse across plasma membrane. In this paper, we describe the design and synthesis of a series of inositol phosphotriester analogues based on phosphatidylinositol, along with the initial antitumor activity analysis. Several compounds exhibited good cytotoxic activity against human cancer cell lines A549, HepG2, MDA-MB-231 and HeLa, especially compound 33 was cytotoxic against all the four cancer cell lines with good IC50 values.
- Song, Fanbo,Zhang, Jing,Zhao, Yuefang,Chen, Wenbin,Li, Luyuan,Xi, Zhen
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experimental part
p. 3642 - 3654
(2012/06/18)
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- Synthesis of the aminocyclitol units of (-)-hygromycin A and methoxyhygromycin from myo-inositol
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Concise and efficient syntheses of the aminocyclitol cores of hygromycin A (HMA) and methoxyhygromycin (MHM) have been achieved starting from readily available myo-inositol. Reductive cleavage of myo-inositol orthoformate to the corresponding 1,3-acetal, stereospecific introduction of the amino group via the azide, and resolution of a racemic cyclitol derivative as its diastereomeric mandelate esters are the key steps in the synthesis. Synthesis of the aminocyclitol core of hygromycin A involved chromatography in half of the total number of steps, and the aminocyclitol core of methoxyhygromycin involved only one chromatography.
- Gurale, Bharat P.,Shashidhar, Mysore S.,Gonnade, Rajesh G.
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experimental part
p. 5801 - 5807
(2012/09/07)
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- Air-stable heterobimetallic catalysts to effect Ni/Cr-mediated couplings with a ca. 1:1 molar ratio of coupling partners at low catalyst loadings
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Two air-stable Ni,Cr-heterobimetallic catalysts have been prepared from ligands 7 and 11, obtained from scyllo-inositol in four and three steps, respectively. Both catalysts smoothly promote Ni/Cr-mediated coupling reactions with a ca. 1:1 molar ratio of coupling partners. The catalyst derived from 11 exhibits a better catalytic profile, thereby allowing Ni/Cr-mediated coupling reactions to be achieved with a wide range of substrates at a low catalyst loading in an operationally simple manner.
- Peng, Jianbiao,Kishi, Yoshito
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supporting information; experimental part
p. 86 - 89
(2012/03/11)
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- A short and efficient route from myo - To neo -inositol
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An efficient route from myo- to neo-inositol is described. The key steps of the sequence are oxidation of the hydroxy group at C-5 to the corresponding ketone, followed by a highly (dr = 7.8:1) stereoselective reduction. The route includes nine steps with an overall yield of 51% and is therefore superior to all hitherto reported methods for the preparation of neo-inositol. Georg Thieme Verlag Stuttgart New York.
- Wessig, Pablo,M?llnitz, Kristian,Hübner, Sebastian
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scheme or table
p. 1497 - 1500
(2010/09/05)
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- The first structural study on a cyclic tricoordinate phosphorochloridite and a pentacoordinate phosphorane based on 1,2,3,5-protected myo-inositol-a new conformation of 1,3,2-dioxaphosphorinane ring
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Treatment of the phosphoramidite {myo-C6H6-2-[OC(O)Ph]-1,3,5-(O3CH)-4,6-(O2P-NH-i-Pr)} with o-chloranil affords the first example of inositol-based pentacoordinate phosphorane {myo-C6H6-2-[
- Pavan Kumar,Kumara Swamy
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p. 1182 - 1188
(2008/02/02)
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- Unified total syntheses of the inositol polyphosphates: D-I-3,5,6P 3, D-I-3,4,5P3, D-I-3,4,6P3, and D-I-3,4,5,6P4 via catalytic enantioselective and site-selective phosphorylation
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Synthetic routes to various inositol polyphosphates have been discovered utilizing catalytic enantioselective and site-selective phosphorylation reactions. The syntheses described herein exploit a common intermediate to gain efficient access to eight unique inositol polyphosphates.
- Morgan, Adam J.,Komiya, Shio,Xu, Yingju,Miller, Scott J.
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p. 6923 - 6931
(2007/10/03)
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- Stereoselective oxidation of protected inositol derivatives catalyzed by inositol dehydrogenase from Bacillus subtilis
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Inositol dehydrogenase (EC 1.1.1.18) from Bacillus subtilis is shown to have a nonpolar cavity adjacent to the active site, allowing racemic protected inositol derivatives such as 4-O-benzyl-myo-inositol to be recognized with very high apparent stereoselectivity.
- Daniellou, Richard,Phenix, Christopher P.,Tam, Pui Hang,Laliberte, Michael C.,Palmer, David R. J.
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p. 401 - 403
(2007/10/03)
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- Establishment of the structure of pinpollitol by total synthesis of the proposed putative structures
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Proposed structures of pinpollitol, namely 1,4-di-O-methyl-chiro-inositol and 1,3-di-O-methyl-chiro-inositol, have been synthesized from myo-inositol. Racemic 1,4-di-O-methyl-chiro-inositol has been synthesized from the readily available 1,2:4,5-di-O-isop
- Sureshan, Kana M.,Murakami, Tomohiro,Watanabe, Yutaka
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p. 769 - 772
(2007/10/03)
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- Molecular evolution using intramolecular acyl migration on myo-inositol benzoates with thermodyamic and kinetic selectors
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A molecular evolution model was successfully demonstrated by combining the intramolecular acyl migration on inositol tribenzoates and boron selectors. The addition of boric acid to 12 members of DCL (dynamic combinatorial library) induced the dramatic amp
- Ahn, Young-Hoon,Chang, Young-Tae
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p. 3543 - 3547
(2007/10/03)
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- Racemic 2,4-di-O-benzoyl-myo-inositol 1,3,5-orthoformate: A versatile intermediate for the preparation of myo-inositol phosphates
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The versatility of racemic 2,4-di-O-benzoyl-myo-inositol 1,3,5- orthoformate as an intermediate for the preparation of protected myo- inositol derivatives is demonstrated. Procedures described provide simple access to several protected myo-inositol derivatives which are intermediates for the preparation of myo-inositol phosphates and racemic ononitol.
- Das, Tanya,Shashidhar, Mysore S.
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p. 165 - 168
(2007/10/03)
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- Syntheses of myo-inositol-1,2,3,5- and 2,4,5,6-tetrakisphosphates, unusual inhibitors of myo-inositol-1,4,5-trisphosphae 3-kinase
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D-myo-Inositol 1,4,5-trisphosphate [D-I(1,4,5)P3], a calcium mobilizing second messenger, is converted to D-I(1,3,4,5)P4 by D-I(1,4,5)P3-3-kinase. Efficient syntheses of I(1,2,3,5)P4 (2) and I(2,4,5,6)P4 (3), novel 3-kinase inhibitors, are reported.
- Chung, Sung-Kee,Chang, Young-Tae
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p. 2715 - 2718
(2007/10/03)
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- Enzyme Assisted Synthesis of Enantiomerically Pure myo-Inositol Derivatives - Chiral Building Blocks for Inositol Polyphosphates
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Using a short and facile synthetic protocol involving highly selective, regio- and enentioselective enzymatic esterifications as key reaction steps, readily available myo-inositol is converted into optically pure 1D-1-O-butyryl-4,6-O-dibenzoyl-myo-inositol (-) - 5, a selectively protected central intermediate for the preparation of numerous inositol phosphates.
- Andersch, P.,Schneider, M. P.
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p. 2135 - 2138
(2007/10/02)
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- The Total Synthesis of myo-Inositol Phosphates via myo-Inositol Orthoformate
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Novel selective alkylations of myo-inositol orthoformate (4) have been used to prepare a series of protected myo-inositol derivatives, (5a-e), (7), (10), (12), and (16).These intermediates have been used in efficient total syntheses of myo-inositol 2-phosphate, (9); myo-inositol 4-phosphate, (6); myo-inositol 1,3-bisphosphate, (18); and myo-inositol 1,3,4,5-tetrakisphosphate (14).This report represents the first total synthesis of the important natural metabolites (14) and (18) and significantly improved methods of preparation of (6) and (9).
- Billington, David C.,Baker, Raymond,Kulagowski, Janusz J.,Mawer, Ian M.,Vacca, Joseph P.,et al.
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p. 1423 - 1429
(2007/10/02)
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