trisodium 3-[bis(3-sulfonatophenyl)phosphino]benzenesulfonate -Drug Synthesis Database

【结构式】

【分子编号】37264

【品名】trisodium 3-[bis(3-sulfonatophenyl)phosphino]benzenesulfonate

【CA登记号】

【分子式】C₁₈H₁₂Na₃O₉PS₃

【分子量】568.428946

【元素组成】C 38.03% H 2.13% Na 12.13% O 25.33% P 5.45% S 16.92%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(II)

The title ternary ligand technetium-99m complex was formed as a mixture of two isomeric forms by reaction of the hydrazinonicotinamide-derivatized cyclic peptide (I) with trisodium triphenylphosphine-3,3',3''-trisulfonate (II) and tricine (III) in the presence of 99mTc pertechnetate and SnCl2. The 99Tc analogue was similarly prepared for spectroscopic characterization by using (n-Bu4N)(99TcOCl4) or (NH4)(99TcO4).

参考文献中间体

合成目标

【1】 Liu, S.; et al.; Technetium complexes of a hydrazinonicotinamide-conjugated cyclic peptide and 2-hydrazinopyridine: synthesis and characterization. Inorg Chem 1999, 38, 6, 1326.
【2】 Liu, S.; Edwards, D.S. (DuPont Pharmaceuticals Co.); Ternary radiopharmaceutical complexes. EP 0995761; US 5744120; WO 9631243 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	48084	2-[(5S,11S,14R)-11-(3-[[amino(imino)methyl]amino]propyl)-19-[(6-[[(6-hydrazino-3-pyridinyl)carbonyl]amino]hexanoyl)amino]-14-isopropyl-12-methyl-4,7,10,13,16-pentaoxo-3,6,9,12,15-pentaazabicyclo[15.3.1]henicosa-1(21),17,19-trien-5-yl]acetic acid	C₃₈H₅₅N₁₃O₉	详情	详情
(II)	37264	trisodium 3-[bis(3-sulfonatophenyl)phosphino]benzenesulfonate	C₁₈H₁₂Na₃O₉PS₃	详情	详情
(III)	37265	4'-(hydroxymethyl)[1,1'-biphenyl]-2-carbonitrile	C₁₄H₁₁NO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

The title compound was then obtained by complexation of hydrazone (IX) with phosphine (II) and tricine (III) in the presence of Na99mTcO4 and SnCl2. Under these conditions, the hydrazone protecting group hydrolyzed to the required hydrazine. Some shortcomings caused by SnCl2 could be omitted using a non-SnCl2-containing formulation in the presence of mannitol and pluronic acid as surfactant agents.

参考文献中间体

合成目标

【1】 Edwards, D.S.; et al.; 99mTc-Labeling of hydrazones of a hydrazinonicotinamide conjugated cyclic peptide. Bioconjugate Chem 1999, 10, 5, 803.
【2】 Liu, S.; et al.; Towards developing A non-SnCl2 formulation for RP444, a new radiopharmaceutical for thrombus imaging. J Pharm Sci 2001, 90, 2, 114.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(II)	37264	trisodium 3-[bis(3-sulfonatophenyl)phosphino]benzenesulfonate	C₁₈H₁₂Na₃O₉PS₃	详情	详情
(III)	37265	4'-(hydroxymethyl)[1,1'-biphenyl]-2-carbonitrile	C₁₄H₁₁NO	详情	详情
(IX)	48090	sodium 2-[[(E)-2-(5-[[(6-[[(4R,7S,13S)-7-(3-[[amino(imino)methyl]amino]propyl)-13-(carboxymethyl)-4-isopropyl-6-methyl-2,5,8,11,14-pentaoxo-3,6,9,12,15-pentaazabicyclo[15.3.1]henicosa-1(21),17,19-trien-19-yl]amino]-6-oxohexyl)amino]carbonyl]-2-pyridinyl)hydrazono]methyl]benzenesulfonate	C₄₅H₅₈N₁₃NaO₁₂S	详情	详情

合成路线3

该中间体在本合成路线中的序号：(III)

The title compound was synthesized from the known formyl tetrapeptide conjugated to 6-hydrazinonicotinic acid (I) by complexation with tricine (II), trisodium triphenylphosphine-3,3',3''-trisulfonate (III) and sodium 99mTc-pertechnetate, either in two steps by first complexation of the stannous chloride-reduced technetium with (I) and (II), and then reaction with (III), or in one step by direct reduction of Na99mTcO4 with SnCl2 in the presence of (I), (II) and (III). The compound was also formed in the absence of SnCl2.

参考文献中间体

合成目标

【1】 Edwards, D.S.; et al.; RP463: A stabilized technetium-99m complex of a hydroazino nicotinamide derivatized chemotactic peptide for infection imaging. Bioconjugate Chem 1999, 10, 5, 884.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	37262	(5S,8S,11S,14S)-11-benzyl-5-(formylamino)-14-(4-[[(6-hydrazino-3-pyridinyl)carbonyl]amino]butyl)-8-isobutyl-6,9,12-trioxo-2-thia-7,10,13-triazapentadecan-15-oic acid		C₃₃H₄₈N₈O₇S	详情	详情
(II)	37263	2-[[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]amino]acetic acid	5704-04-1	C₆H₁₃NO₅	详情	详情
(III)	37264	trisodium 3-[bis(3-sulfonatophenyl)phosphino]benzenesulfonate		C₁₈H₁₂Na₃O₉PS₃	详情	详情

Extended Information