CAS: 17094-01-8; (S)-2-Amino-6-(2-Hydroxypropanoyl)-7,8-Dihydropteridin-4(3H)-One

该化合物是一种生物活性雌激素化合物,是四氢生物激素(BH4)生物合成的关键中间体,是氮氧化物合成物和芳香氨基氨基酸氢氧基酶的基本共生物,其高纯度和稳定性使它成为研究酶学,...

结构式图片

合成工艺路线路线简述

  • 合成目标产物 L-Sepiapterin 主要起始原料 6-Pteridinemethanol, 2-Amino-4-(Cyclohexyloxy)-α-[(1S)-1-(Methoxymethoxy)Ethyl]-, (αr)-
  • (文献来源)合成步骤主要原料 6-Pteridinemethanol, 2-Amino-4-(Cyclohexyloxy)-α-[(1S)-1-(Methoxymethoxy)Ethyl]-, (αr)-
1-(2-Amino-4-Cyclohexyloxy-7,8-Dihydropteridin-6-yl)-2S-2-(Methoxymethoxy)Propan-1-One置于盐酸,Sodium Hydroxide体系中,用 水 用作溶剂,化学反应生成L-墨蝶呤
参考文献:Method For Producing Sepiapterin And Tetrahydrolactoylpterin
标题:Method For Producing Sepiapterin And Tetrahydrolactoylpterin

海关参考信息

专利信息


专利号:US-5401844-A
优先权日:1983-04-11
标 题 :Regulation of enzymes which utilize tetrahydrobiopterin or tetrahydrofolate cofactors with 6,6-disubstituted-tetrahydropteridines
发明人:AYLING JUNE E; BAILEY STEVEN W
权利人:UNIV SOUTH ALABAMA
摘要:6-[2'-Amino-2',2'-disubstituted-ethylamino]-pyrimidines of the structure: ##STR1## in which X=H, NH 2 or NO 2 , which are novel intermediates in the synthesis of quinoid 6,6-disubstituted-dihydro- and 6,6-disubstituted-tetrahydro-pteridines, are claimed.

专利号:US-6153615-A
优先权日:1991-12-26
标 题 :Blocking induction of tetrahydrobioterin to block induction of nitric oxide synthesis
发明人:GROSS STEVEN S
权利人:CORNELL RES FOUNDATION INC
摘要:Guanosine triphosphate pathway tetrahydrobiopterin synthesis antagonist and/or pterin salvage pathway tetrahydrobiopterin synthesis antagonists are administered to inhibit nitric oxide synthesis from arginine in vascular cells in a subject in need of such inhibition (e.g., for prophylactic or curative effect for endotoxin- or cytokine-induced hypotension or for restoration of vascular contractile sensitivity to pressor agents in the treatment of such hypotension). The tetrahydrobiopterin synthesis antagonist may be administered with α 1 -adrenergic agonist or with nitric oxide synthase inhibitor. The tetrahydrobiopterin synthesis antagonists are also administered to attenuate inflammation caused by induced nitric oxide production in immune cells. Unwanted counterproductive or side effects can be eliminated or ameliorated by administration additionally of levodopa with or without carbidopa and L-5-hydroxytryptophane.

专利号:US-6274581-B1
优先权日:1991-12-26
标 题 :Blocking induction of tetrahydrobiopterin to block induction of nitric oxide synthesis
发明人:GROSS STEVEN S
权利人:CORNELL RES FOUNDATION INC
摘要:Guanosine triphosphate pathway tetrahydrobiopterin synthesis antagonist and/or pterin salvage pathway tetrahydrobiopterin synthesis antagonist are administered to inhibit nitric oxide synthesis from arginine in vascular smooth muscle cells in a subject in need of such inhibition (e.g. for prophylactic or curative effect for cytokine-induced hypotension or for restoration of vascular contractile sensitivity to pressor agents in the treatment of such hypotension).

专利号:US-6844343-B1
优先权日:1999-09-17
标 题 :N-substituted 4-aminopteridines, synthesis and use thereof as pharmaceutical agent
发明人:PFLEIDERER WOLFGANG; SCHMIDT HARALD; FROEHLICH LOTHAR; KOTSONIS PETER; TAGHAVI-MOGHADAM SHAHRIYAR
权利人:VASOPHARM BIOTECH GMBH
摘要:Compounds of formula (I), where preferably: A=a bridge of partial formula (II) or (III), R<1 >and R<2>=independently (substituted) alkyl, aryl or aralkyl, or together form a heterocycle, R<3>=H, -CO-Alkyl, or -CO-Aryl, R<4>=Aryl, -CO-O-Aryl or -CO-Aryl and R<5>=H, are potent inhibitors of NO-synthase and are suitable as pharmaceutical agents of prophylaxis and treatment of disease states associates with a disturbed NO metabolism.

专利号:JP-H06316576-A
优先权日:1983-04-11
标题 :Synthesis of 6,6-di-substituted dihydropteridine

专利号:US-5877176-A
优先权日:1991-12-26
标题 :Blocking induction of tetrahydrobiopterin to block induction of nitric oxide synthesis
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CAS号:17094-01-8
中文名:L-墨蝶呤
英文名:L-SEPIAPTERIN
纯度:99% HPLC1G/5G/1KG
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主要参考文献


1: Sumi-Ichinose C, Suganuma Y, Kano T, Ikemoto K, Ihira N, Ichinose H, Kondo K. Priapism caused by partial deficiency of tetrahydrobiopterin through hypofunction of the sympathetic neurons in sepiapterin reductase gene-disrupted mice. J Inherit Metab Dis. 2022 Feb 22. doi: 10.1002/jimd.12489. Epub ahead of print. 13(3):749-754. doi: 10.1159/000520436.
4: Wang W, Zheng Q, Yu C, Pan C, Luo P, Chen J. WSV056 Inhibits Shrimp Nitric Oxide Synthase Activity by Downregulating Litopenaeus vannamei Sepiapterin Reductase to Promote White Spot Syndrome Virus Replication. Front Microbiol. 2021 Dec 23;12:796049. doi: 10.3389/fmicb.2021.796049.
5: Bratkovic D, Margvelashvili L, Tchan MC, Nisbet J, Smith N. PTC923 (sepiapterin) lowers elevated blood phenylalanine in subjects with phenylketonuria: a phase 2 randomized, multi-center, three-period crossover, open-label, active controlled, all-comers study. Metabolism. 2022 Mar;128:155116. doi: 10.1016/j.metabol.2021.155116. Epub 2021 Dec 29. 11(11):1186. doi: 10.3390/jpm11111186.

合成参考文献


摘要:
摘要:Kleemann A., Kutscher B., Reichert D., Bossart M., Pharmaceutical Substances, Thieme [Online], Stuttgart, (2026).
参考文献:10.1021/bi0302191
摘要:Boissel JP, Bros M, Schröck A, Gödtel-Armbrust U, Förstermann U. Cyclic AMP-mediated upregulation of the expression of neuronal NO synthase in human A673 neuroepithelioma cells results in a decrease in the level of bioactive NO production: analysis of the signaling mechanisms that are involved. Biochemistry. 2004 Jun 08;43(22):7197–206. doi: 10.1021/bi0302191.
参考文献:10.1161/01.res.0000231306.03510.77
摘要:Elrod JW, Duranski MR, Langston W, Greer JJ, Tao L, Dugas TR, Kevil CG, Champion HC, Lefer DJ. eNOS gene therapy exacerbates hepatic ischemia-reperfusion injury in diabetes: a role for eNOS uncoupling. Circ Res. 2006 Jul 07;99(1):78–85. doi: 10.1161/01.res.0000231306.03510.77.
参考文献:10.1007/s11306-021-01861-9
摘要:Rasmussen L, Foulks Z, Burton C, Shi H. Establishing pteridine metabolism in a progressive isogenic breast cancer cell model. Metabolomics. 2021 Dec 17;18(1):2.
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