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ChemicalBook CAS DataBase List Suramin sodium
129-46-4

Suramin sodium synthesis

1synthesis methods
Suramin, a hexasodium salt of [8,8’ carbonyl-bis-[imino-3,1-phenylencarbonylimino(4-methyl-3,1-phenylen)carbonylimino]]-bis-1,3,5-naphthalintrisulfonic acid (37.4.13), can be made by reacting 1-aminonaphthalene-3,6,8-trisulfonic acid with 4-methyl-3-nitrobenzoyl chloride to make a nitrobenzoic derivative (37.4.8). The nitro group in this compound is reduced by activated iron to an amino derivative (37.4.9), which is acylated by m-nitrobenzoylchloride to make a new nitroderivative, m-nitrobenzoyl-(4-methyl-3-aminobenzoyl)-1-aminonaphthalene-3,6,8-trisulfonic acid (37.4.10).
This is once again reduced to the amine (37.4.11) in the same manner. Reacting the resulting product with phosgene makes [8,8′-carbonyl-bis-[imino-3,1-phenylencarbonylimino(4-methyl-3,1-phenylen]-carbonylimino]-bis-1,3,5-naphthalenetrisulfonic acid (37.4.12), which upon being treated with sodium hydroxide gives suramin.

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Yield:-

Steps:

Multi-step reaction with 5 steps
1: 88.1 percent / toluene; H2O / pH 4
2: 95.6 percent / H2 / Pd/C / H2O
3: 68.8 percent / toluene; H2O / pH 4
4: 85.3 percent / H2 / Pd/C / H2O
5: toluene; H2O / pH 4

References:

Ullmann, Heiko;Meis, Sabine;Hongwiset, Darunee;Marzian, Claudia;Wiese, Michael;Nickel, Peter;Communi, Didier;Boeynaems, Jean-Marie;Wolf, Christian;Hausmann, Ralf;Schmalzing, Günther;Kassack, Matthias U. [Journal of Medicinal Chemistry,2005,vol. 48,# 22,p. 7040 - 7048]

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