1,4,7,10-tetraoxo-1-phenyl-2-thia-5,8,11-triazatridecan-13-oic acid -Drug Synthesis Database

【结构式】

【分子编号】56520

【品名】1,4,7,10-tetraoxo-1-phenyl-2-thia-5,8,11-triazatridecan-13-oic acid

【CA登记号】

【分子式】C₁₅H₁₇N₃O₆S

【分子量】367.3826

【元素组成】C 49.04% H 4.66% N 11.44% O 26.13% S 8.73%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IV)

The benzoyl-protected ligand (IV) was prepared as follows. Acylation of triglycine (I) with chloroacetyl chloride (II) produced the chloroacetamide (III). Subsequent treatment of chloride (III) with sodium thiobenzoate yielded thioester (IV). The title 99technetium complex was prepared by in situ hydrolysis of the thiobenzoate ester (IV) to mercaptoacetyl triglycine (V) in the presence of a solution of [99mTc]pertechnetate, SnCl2 as the technetium reducing species, and gluconate or tartrate as intermediate Tc complexing agents.

参考文献中间体

合成目标

【1】 Hung, J.C.; et al.; Rapid preparation and quality control of technetium-99m MAG3(TM). J Nucl Med Technol 1991, 19, 3, 176.
【2】 Reyes-Herrera, L.; et al.; An alkaline kit formulation to obtain [99mTc]MAG3 in high radiochemical yields. J Radioanal Nucl Chem 1995, 199, 6, 507.
【3】 Grummon, G.; et al.; Synthesis, characterization and crystal structures of technetium(V)-oxo complexes useful in nuclear medicine. 1. Complexes of mercaptoacetylglycylglycylglycine (MAG3) and its methyl ester derivative (MAG3OMe). Inorg Chem 1995, 34, 7, 1764.
【4】 Fritzburg, A. (University of Utah); Radiolabeled technetium chelates for use in renal function determinations. EP 0173424 .
【5】 Fritzberg, A.R.; Kasina, S.; Eshima, D.; Johnson, D.L.; Synthesis and biological evaluation of technetium-99m MAG3 as a hippuran replacement. J Nucl Med 1986, 27, 1, 111.
【6】 Brandau, W.; et al.; Technetium-99m labeled renal function and imaging agents. 3. Synthesis of Tc-99m-MAG3 and biodistribution of by-products. Int J Radiat Appl Instrum Part A - Appl Radiat Isotop 1988, 39, 2, 121.

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)	56518	2-({2-[(2-aminoacetyl)amino]acetyl}amino)acetic acid		C₆H₁₁N₃O₄	详情	详情
(II)	11296	2-Chloroacetyl chloride; Chloroacetic chloride	79-04-9	C₂H₂Cl₂O	详情	详情
(III)	56519	2-{[2-({2-[(2-chloroacetyl)amino]acetyl}amino)acetyl]amino}acetic acid		C₈H₁₂ClN₃O₅	详情	详情
(IV)	56520	1,4,7,10-tetraoxo-1-phenyl-2-thia-5,8,11-triazatridecan-13-oic acid		C₁₅H₁₇N₃O₆S	详情	详情
(V)	56521	2-{[2-({2-[(2-sulfanylacetyl)amino]acetyl}amino)acetyl]amino}acetic acid		C₈H₁₃N₃O₅S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

The protected ligand (IV) was also prepared by a related method. The acylation of thioglycolic acid (V) with benzoyl chloride (VI) under Schotten-Baumann conditions afforded S-benzoyl thioglycolic acid (VII). After activation of (VII) as the corresponding succinimidyl ester (VIII) with N-hydroxysuccinimide and DCC, coupling with triglycine (I) furnished compound (IV).

参考文献中间体

合成目标

【1】 Grummon, G.; et al.; Synthesis, characterization and crystal structures of technetium(V)-oxo complexes useful in nuclear medicine. 1. Complexes of mercaptoacetylglycylglycylglycine (MAG3) and its methyl ester derivative (MAG3OMe). Inorg Chem 1995, 34, 7, 1764.
【2】 Brandau, W.; et al.; Technetium-99m labeled renal function and imaging agents. 3. Synthesis of Tc-99m-MAG3 and biodistribution of by-products. Int J Radiat Appl Instrum Part A - Appl Radiat Isotop 1988, 39, 2, 121.

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)	56518	2-({2-[(2-aminoacetyl)amino]acetyl}amino)acetic acid		C₆H₁₁N₃O₄	详情	详情
(IV)	56520	1,4,7,10-tetraoxo-1-phenyl-2-thia-5,8,11-triazatridecan-13-oic acid		C₁₅H₁₇N₃O₆S	详情	详情
(V)	18524	2-sulfanylacetic acid	68-11-1	C₂H₄O₂S	详情	详情
(VI)	10463	Benzoyl chloride	98-88-4	C₇H₅ClO	详情	详情
(VII)	56522	2-(benzoylsulfanyl)acetic acid		C₉H₈O₃S	详情	详情
(VIII)	56523	S-{2-[(2,5-dioxo-1-pyrrolidinyl)oxy]-2-oxoethyl} benzenecarbothioate		C₁₃H₁₁NO₅S	详情	详情

Extended Information