227177-05-1Relevant articles and documents
Synthesis and in vitro anticancer activity evaluation of novel bioreversible phosphate inositol derivatives
Chen, Wenbin,Deng, Zhaohui,Chen, Kuangyu,Dou, Daolei,Song, Fanbo,Li, Luyuan,Xi, Zhen
supporting information, p. 172 - 181 (2015/03/05)
The chemistry and biology of phosphorylated inositols have become intense areas of research during the last two decades due to their involvement in various cellular signaling processes. However, the metabolic instability by phosphatases or kinases and poo
Synthesis and antitumor activity of inositol phosphotriester analogues
Song, Fanbo,Zhang, Jing,Zhao, Yuefang,Chen, Wenbin,Li, Luyuan,Xi, Zhen
, p. 3642 - 3654 (2012/06/18)
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.
Intramolecular hydrogen abstraction in radicals derived from inositol 1,3-acetals: Efficient access to cyclitols
Murali, Chebrolu,Gurale, Bharat P.,Shashidhar, Mysore S.
experimental part, p. 755 - 764 (2010/03/26)
The benzylidene acetals obtained by cleavage of the orthobenzoate moiety in myoinositol 1,3,5-orthobenzoate were used to prepare mono- as well as di-deoxy inositol derivatives via their xanthates. The dideoxygenation is a result of intramolecular abstraction of the benzylidene acetal hydrogen and subsequent cleavage of the acetal ring. Such a cleavage does not take place in analogous acetals derived from, other orthoesters. The 1, 3-acetals derived from, myo- inositol 1,3,5-orthoesters were also used to prepare neo-inositol and isomeric deoxy-amino inositols. Most of the reactions in these synthetic sequences starting from myo-inositol give one product in each step. The results presented here show that myo-inositol 1,3,5-orthobenzoate offers many advantages over other orthoesters for the synthesis of cyclitol derivatives from myo-inositol.
Synthesis and biological evaluation of phosphatidylinositol phosphate affinity probes
Conway, Stuart J.,Gardiner, James,Grove, Simon J. A.,Johns, Melloney K.,Lim, Ze-Yi,Painter, Gavin F.,Robinson, Diane E. J. E.,Schieber, Christine,Thuring, Jan W.,Wong, Leon S.-M.,Yin, Meng-Xin,Burgess, Antony W.,Catimel, Bruno,Hawkins, Phillip T.,Ktistakis, Nicholas T.,Stephens, Leonard R.,Holmes, Andrew B.
scheme or table, p. 66 - 76 (2010/04/29)
The synthesis of the complete family of phosphatidylinositol phosphate analogues (PIPs) from five key core intermediates A-E is described. These core compounds were obtained from myo-inositol orthoformate 1 via regioselective DIBAL-H and trimethylaluminium-mediated cleavages and a resolution-protection process using camphor acetals 10. Coupling of cores A-E with phosphoramidites 34 and 38, derived from the requisite protected lipid side chains, afforded the fully-protected PIPs. Removal of the remaining protecting groups was achieved via hydrogenolysis using palladium black or palladium hydroxide on carbon in the presence of sodium bicarbonate to afford the complete family of dipalmitoyl- and amino-PIP analogues 42, 45, 50, 51, 58, 59, 67, 68, 76, 77, 82, 83, 92, 93, 99 and 100. Investigations using affinity probes incorporating these compounds have identified novel proteins involved in the PI3K intracellular signalling network and have allowed a comprehensive proteomic analysis of phosphoinositide interacting proteins. The Royal Society of Chemistry 2010.
General synthesis of 3-phosphorylated mj'o-inositol phospholipids and derivatives
Painter, Gavin F.,Grove, Simon J. A.,Gilbert, Lan H.,Holmes, Andrew B.,Raithby, Paul R.,Hill, Malcolm L.,Hawking, Phillip T.,Stephens, Leonard R.
, p. 923 - 935 (2007/10/03)
The D-3-phosphorylated wyo-inositol phospholipids PtdIns(3)P, PtdIns(3,4)P2, PtdIns(3,4,5)P3 and PtdIns(3,5)P2 were synthesised from /yo-inositol orthoformate 8. Key transformations included the regioselective DIBAL- and trimethylaluminium-mediated cleavages of wiyo-inositol orthoformate intermediates and a resolution-protection protocol using the camphor acetals 17. The final reductive debenzylation was effected with Pearlman's catalyst [Pd(OH)J in the presence of sodium hydrogen carbonate. The biological properties of the phospholipids were evaluated against various protein kinases (PKB and PDK-1) in which they played an important activation role.
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
Schmitt, Laurent,Spiess, Bernard,Schlewer, Gilbert
, p. 4817 - 4820 (2007/10/03)
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.
Lewis acid-catalysed rearrangement of myo-inositol orthoformate derivatives
Gilbert, Ian H.,Holmes, Andrew B.,Pestchanker, Mauricio J.,Young, Rodney C.
, p. 117 - 130 (2007/10/02)
Reduction of 2,4,6-tri-O-benzyl-DL-myo-inositol 1,3,5-orthoformate (1) with di-isobutylaluminium hydride gave 2,4,6-tri-O-benzyl-1,3-O-methylene-DL-myo-inositol (2), whereas reaction with trimethylaluminium gave 2,4,6-tri-O-benzyl-1,5-O-ethylidene-DL-myo-
SYNTHESIS OF PROTECTED myo-INOSITOLS
Gilbert, Ian H.,Holmes, Andrew B.,Young, Rodney C.
, p. 2633 - 2634 (2007/10/02)
Regioselective cleavages of the myo-inositol monoorthoformate (2) and a rearrangement of the acetal (5) are reported.
