144773-26-2|Cyclophostin|(3R,8aR)-3-Methoxy-5-methyl-3-oxo-8,8a-dihydro-1H-furo[3,4-e][1,3,2]dioxaphosphepin-6-one|-范德生物科技公司

Cyclophostin

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names：
(3R,8aR)-3-Methoxy-5-methyl-3-oxo-8,8a-dihydro-1H-furo[3,4-e][1,3,2]dioxaphosphepin-6-one
CAS号：
144773-26-2
MDL Number：
MF(分子式)： C8H11O6P MW(分子量)： 234.14
EINECS: Reaxys Number:
Pubchem ID: Brand:BIOFOUNT

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中文别名	Cyclophostin
英文别名	Cyclophostin;
CAS号	144773-26-2
SMILES	O=C1OC[C@]2([H])CO[P@](OC(C)=C21)(OC)=O
Inchi	InChI=1S/C8H11O6P/c1-5-7-6(3-12-8(7)9)4-13-15(10,11-2)14-5/h6H,3-4H2,1-2H3/t6-,15-/m1/s1
InchiKey	OMPQJMDGDAAXPE-NPMWZIQKSA-N
分子式 Formula	C8H11O6P
分子量 Molecular Weight	234.14
闪点 FP
熔点 Melting point
沸点 Boiling point
Polarizability极化度
密度 Density
蒸汽压 Vapor Pressure
溶解度Solubility
性状	Solid powder
储藏条件 Storage conditions	Dry, dark and store at 0-4℃ for short term (days to weeks) or -20℃ for long term (Store correctly 2-3years).

产品说明	Cyclophostin(CAS:144773-26-2):仅限应用于工业或者科学研究过程中非医疗目的，不应用于人类或动物的临床诊断以及治过程疗，该产品非药用，非食用。
Introduction	Cyclophostin is an irreversible inhibitor of acetylcholinesterase (AChE).
Application1
Application2
Application3

警示图
危险性	Warning
危险性警示
安全声明
安全防护
备注

[1]Viljoen A, Richard M, Nguyen PC, Fourquet P, Camoin L, Paudal RR, Gnawali GR, Spilling CD, Cavalier JF, Canaan S, Blaise M, Kremer L. Cyclipostins and Cyclophostin analogs inhibit the antigen 85C from Mycobacterium tuberculosis both in vitro and in vivo. J Biol Chem. 2018 Jan 4. pii: jbc.RA117.000760. doi: 10.1074/jbc.RA117.000760. [Epub ahead of print] PubMed PMID: 29301937.

[2]Nguyen PC, Madani A, Santucci P, Martin BP, Paudel RR, Delattre S, Herrmann JL, Spilling CD, Kremer L, Canaan S, Cavalier JF. Cyclophostin and cyclipostins analogs, new promising molecules to treat mycobacterial-related diseases. Int J Antimicrob Agents. 2017 Dec 11. pii: S0924-8579(17)30435-1. doi: 10.1016/j.ijantimicag.2017.12.001. [Epub ahead of print] PubMed PMID: 29241819.

[3] Nguyen PC, Delorme V, Bénarouche A, Martin BP, Paudel R, Gnawali GR, Madani A, Puppo R, Landry V, Kremer L, Brodin P, Spilling CD, Cavalier JF, Canaan S. Cyclipostins and Cyclophostin analogs as promising compounds in the fight against tuberculosis. Sci Rep. 2017 Sep 18;7(1):11751. doi: 10.1038/s41598-017-11843-4. PubMed PMID: 28924204; PubMed Central PMCID: PMC5603573.

[4] Martin BP, Vasilieva E, Dupureur CM, Spilling CD. Synthesis and comparison of the biological activity of monocyclic phosphonate, difluorophosphonate and phosphate analogs of the natural AChE inhibitor cyclophostin. Bioorg Med Chem. 2015 Dec 15;23(24):7529-34. doi: 10.1016/j.bmc.2015.10.044. Epub 2015 Oct 30. PubMed PMID: 26585276.

[5] Vasilieva E, Dutta S, Malla RK, Martin BP, Spilling CD, Dupureur CM. Rat hormone sensitive lipase inhibition by cyclipostins and their analogs. Bioorg Med Chem. 2015 Mar 1;23(5):944-52. doi: 10.1016/j.bmc.2015.01.028. Epub 2015 Jan 22. PubMed PMID: 25678014; PubMed Central PMCID: PMC4340684.

6: Point V, Malla RK, Carrière F, Canaan S, Spilling CD, Cavalier JF. Enantioselective inhibition of microbial lipolytic enzymes by nonracemic monocyclic enolphosphonate analogues of cyclophostin. J Med Chem. 2013 Jun 13;56(11):4393-401. doi: 10.1021/jm4000787. Epub 2013 May 16. PubMed PMID: 23651298.7: Point V, Malla RK, Diomande S, Martin BP, Delorme V, Carriere F, Canaan S, Rath NP, Spilling CD, Cavalier JF. Synthesis and kinetic evaluation of cyclophostin and cyclipostins phosphonate analogs as selective and potent inhibitors of microbial lipases. J Med Chem. 2012 Nov 26;55(22):10204-19. doi: 10.1021/jm301216x. Epub 2012 Nov 7. PubMed PMID: 23095026; PubMed Central PMCID: PMC3518039.8: Malla RK, Bandyopadhyay S, Spilling CD, Dutta S, Dupureur CM. The first total synthesis of (±)-cyclophostin and (±)-cyclipostin P: inhibitors of the serine hydrolases acetyl cholinesterase and hormone sensitive lipase. Org Lett. 2011 Jun 17;13(12):3094-7. doi: 10.1021/ol200991x. Epub 2011 May 17. PubMed PMID: 21591624; PubMed Central PMCID: PMC3129627.9: Dutta S, Malla RK, Bandyopadhyay S, Spilling CD, Dupureur CM. Synthesis and kinetic analysis of some phosphonate analogs of cyclophostin as inhibitors of human acetylcholinesterase. Bioorg Med Chem. 2010 Mar 15;18(6):2265-74. doi: 10.1016/j.bmc.2010.01.063. Epub 2010 Feb 4. PubMed PMID: 20189400; PubMed Central PMCID: PMC2841358.10: Bandyopadhyay S, Dutta S, Spilling CD, Dupureur CM, Rath NP. Synthesis and biological evaluation of a phosphonate analog of the natural acetyl cholinesterase inhibitor cyclophostin. J Org Chem. 2008 Nov 7;73(21):8386-91. doi: 10.1021/jo801453v. Epub 2008 Sep 27. PubMed PMID: 18821801; PubMed Central PMCID: PMC2726048.1

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