Reference

Modulation of animal cellular responses with compositions containing 8-substituted guanine derivatives

Modulation of animal cellular responses with compositions containing 8-substituted guanine derivatives. Goodman, Michael G.; Weigle, William O. (Scripps Clinic and Research Foundation, USA). PCT Int. Appl. WO 8401898 A1 24 May 1984, 128 pp. DESIGNATED STATES: W: AU, DK, FI, JP, NO. (English). (World Intellectual Property Organization). CODEN: PIXXD2. CLASS: IC: A61K045-02; A61K031-70; C12P021-00. APPLICATION: WO 83-US1722 7 Nov 1983. PRIORITY: US 82-439846 9 Nov 1982; US 83-546679 1 Nov 1983. DOCUMENT TYPE: Patent CA Section: 63 (Pharmaceuticals) Section cross-reference(s): 15 Animal cellular responses are modulated with oral or parenteral compds. contg. 8-substituted guanines bonded 9-1' to an aldose having 5 or 6 C atoms in the aldose chain. The guanines are free of charged functional groups and the 8-substituent has an electron withdrawing inductive effect greater than that of hydrogen. Tablets were prepd. contg. 8-bromoguanosine [4016-63-1] 5.0, lactose 35.4, corn starch 33.0, finely divided silica 5.6, poly(vinylpyrrolidone) 0.6, and Mg stearate 0.4 parts by wt. Enhancement of the primary antibody response by the guanine derivs. was demonstrated.

8,2'-O-Cycloguanosine

8,2'-O-Cycloguanosine. Ikehara, Morio; Maruyama, Tokumi (Sankyo Co., Ltd., Japan). Japan. Kokai JP 51054586 13 May 1976 Showa, 6 pp. (Japanese). 4016-63-1 and 56845-07-9 are cas registry numbers. These chemicals are also mentioned in this article. (Japan). CODEN: JKXXAF. CLASS: IC: C07H019-16. APPLICATION: JP 74-127345 5 Nov 1974. DOCUMENT TYPE: Patent CA Section: 33 (Carbohydrates) Section cross-reference(s): 28, 63 8-Bromoguanosine (I) was treated with Bu2SnO to give 2',3'-O-dibutylstannylene deriv. Sulfonylation in the presence of an org. base gave 8-bromo-2'-sulfonylguanosine deriv. (II). Heating II with an org. acid and org. acid salt, followed by heating with a catalyst gave 8,2'-O-cycloguanosine (III). Thus, 283 mg I was heated with Bu2SnO in MeOH for 1 hr. After cooling, Et3N and tosyl chloride were added and the mixt. was stirred for 10 min to give 278 mg 8-bromo-2'-O-tosylguanosine, 1.548 g of which was added to a mixt. of AcONa, Ac2O, and AcOH, and refluxed for 4 hr to give 1.1 g 8-hydroxy compd., 1.0 g of which was dissolved in DMF and heated for 4 hr with AcONa to give 376 mg III. .