6670. Noformicin

Nomenclature

CAS number: 155-38-4
5-Amino-N-(3-amino-3-iminopropyl)-3,4-dihydro-2H-pyrrole-2-carboxamide; N-(2-amidinoethyl)-5-imino-2-pyrrolidinecarboxamide; 2-[N-(2-amidinoethyl)carbamoyl]-5-iminopyrrolidine; β-(5-imino-2-pyrrolidinecarboxamido)propamidine; noformycin.
C8H15N5O; mol wt 197.24.
C 48.72%, H 7.67%, N 35.51%, O 8.11%.

Description and references

Antiviral agent produced by Nocardia formica, culture no. N.R.R.L. 2470: Peck et al., US 2804463 (1957 to Merck & Co.); Gray, Phytopathology 45, 281 (1955). Activity studies: Furusawa et al., Proc. Soc. Exp. Biol. Med. 116, 938 (1964); eidem, Med. Pharmacol. Exp. 12, 259 (1965). Synthesis of (+)- and (±)-forms: Diana, J. Med. Chem. 16, 857 (1973).

Chemical structure

Derivative

(+)-Form dihydrochloride.
C8H17Cl2N5O; mol wt 270.16.
C 35.57%, H 6.34%, Cl 26.25%, N 25.92%, O 5.92%.

Properties

The biologically active form. Crystals from methanol, dec 263-264°. [α]D25 +8.8° (methanol). Sol in water. Somewhat sol in organic solvents. pKa 9.4.

Derivative

(±)-Form dihydrochloride.

Properties

mp 252-254°.