- 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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- 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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- 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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- 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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- Synthesis of 1-O-(2-oxo-benzo-1,3,2-dioxaphosphaocan-2-yl)-myo-inositol and 3,5-dideoxy-1-O-(2-oxo-benzo-1,3,2-dioxaphosphaocan-2-yl)-myo-inositol as prodrugs of inositolmonophosphatase ligands
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1-O-(2-oxo-benzo-1,3,2-dioxaphosphaocan-2-yl)-myo-inositol and 3,5- dideoxy-1-O-(2-oxo-benzo-1,3,2-dioxaphosphaocan-2-yl)-myo-inositol were prepared by selective modifications of myo-inositol. Phosphorylation used the phosphite method by means of the 2(N,N-di-isopropylamino)-benzo-1,3,2- dioxaphosphaocane.
- Schmitt, Laurent,Spiess, Bernard,Schlewer, Gilbert
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p. 4817 - 4820
(2007/10/03)
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- STUDIES ON ORGANOPHOSPHORUS COMPOUNDS 58. SYNTHESIS OF myo-INOSITOL-1,3,5-O-PHOSPHATE AS A NEW TYPE OF CAGE-PHOSPHATE
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A new type of a cage-phosphate with resemblance to the adamantane structure namely myo-inositol-1,2,5-O-phosphate was synthesized by debenzylation of 2,4,6-O-tribenzyl-myo-inositol-1,3,5-O-phosphate, which was obtained either by direct phosphorylation of
- Yuan, Chengye,Zhai, Haixiao,Li, Yubao,Wang, Sanshan
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- Total synthesis of new 1,5-bissubstituted myo-inositol derivatives. Synthesis of D-myo-inositol 1,5-bisphosphate, 3,5-bisphosphate and of rac. 1,5-Bissulphated and 1,5-bissulphamoylated isosteric analogues
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Convenient synthesis of D-myo-inositol 1,5-bisphosphate, 3,5-bisphosphate and isosteric rac. 1,5-bissulphate and 1,5-bissulphonamide was accomplished from key intermediate 2,3,4,6-tetra-O-benzyl-myo-inositol.
- Westerduin, Pieter,Willems, Henrica A. M.,Van Boeckel, Constant A. A.
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p. 6915 - 6918
(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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