8-Azatheophylline and its derivatives as coronary vasodilators

Abstract

Notes C=0), 3100 and 3250 cm-1 (NH)] was prepd from 1, C1CH2-COC1, and NEta in PhH.A mixt of 25 g (0.135 mole) of potassium phthalimide and 25 g (0.11 mole) of A'-chloroacetyl-l-aminoadamantane in 100 ml of DMF was stirred at 80°for 5 hr. The mixt was distributed between CHCls and H20. The CHCla ext was washed with 0.2 N NaOH soln, dried (Na2S04), and evapd. The residue was triturated with Et20 to give crystals. These were filtered off to give 36.5 g (98%) of A7-(phthalylglycyl)-l-aminoadamantane: mp 233-235°; ir (Nujol), 1655 cm-1 (amide C=0), 1720 and 1770 cm-1 (phthalimide carbonyls), 3300 cm-1 (NH). Recrystn (MeOH) raised the mp, 237.9-239.5°.A mixt of 29.0 g (0.092 mole) of A7-(phthalylgly cyl)-l-aminoadamantane and 10 ml of 100% hydrazine hydrate in 200 ml of EtOH was refluxed for 2 hr. The mixt was evapd to dryness, and the residue was digested in 1200 ml of 2 A7 HC1 at 50°for 10 min. The solid was removed by filtration, and the filtrate was treated with 10% NaOH soln until pptn was complete. The solid was extd with Et20. The Et20 was evapd to give 18 g of residue. A 3-g portion of residue was recrystd (H20) to give Nglycyl-l-aminoadamantane, mp 131-133°. Treatment with HC1 in Et20 gave 81.4-( 1-Adamantyl)semicarbazide ( 82).-A mixt of 3.54 g (0.020 mole) of 1-adamantane isocyanate33 and 10 ml (10 g, 0.31 mole) of anhyd hydrazine in 15 ml of DMF was allowed to stand for 30 min. The mixt was poured into 100 ml of H20. The ppt was (33) H. Stetter and C.

6-Isopropyl-5-methoxy-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one

“…Fpr the biological activity of 8-azaguanine derivatives, see: Roblin et al (1945); Ding et al (2004); Mitchell et al (1950); Levine et al (1963); Montgomery et al (1962); Yamamoto et al (1967); Bariana (1971); Holland et al (1975). For related structures, see: Chen & Shi (2006); Ferguson et al (1998); Li et al (2004); Maldonado et al (2006); Wang et al (2006); Xiao & Shi (2007); Zeng et al (2006Zeng et al ( , 2009 Table 1 Hydrogen-bond geometry (Å , ).…”

“…The derivatives of heterocycles containing 8-azaguanine system, which are well known bioisosteres of guanine, are of great importance because of their remarkable biological properties, such as antimicrobial or antifungal activities (Roblin et al, 1945;Ding et al, 2004), encephaloma cell inhibitor (Mitchell et al, 1950;Levine et al, 1963), antileukemie (Montgomery et al, 1962), hypersusceptibility inhibitor and acesodyne activities (Yamamoto et al, 1967;Bariana, 1971;Holland et al, 1975).…”

Ethyl 1-benzyl-5-{[(isopropylamino)(3-nitrophenoxy)methylidene]amino}-1H-1,2,3-triazole-4-carboxylate

“…For the biological activity of 8-azaguanine derivatives, see: Roblin et al (1945); Ding et al (2004); Mitchell et al (1950); Levine et al (1963); Montgomery et al (1962); Yamamoto et al (1967); Bariana (1971); Holland et al (1975). For related structures, see: Chen & Shi (2006); Ferguson et al (1998); Li et al (2004); Maldonado et al (2006); Wang et al (2006); Xiao & Shi (2007); Zeng et al (2006Zeng et al ( , 2009 ;Zhao, Hu et al (2005); Zhao, Wang & Ding (2005) ;Zhao, Xie et al (2005).…”

“…Some of these activities include antimicrobial or antifungal activities (Roblin et al, 1945;Ding et al, 2004), encephaloma cell inhibitor activity (Mitchell et al, 1950;Levine et al, 1963), antileukemie activity (Montgomery et al, 1962), hypersusceptibility inhibitor activity and acesodyne activity (Yamamoto et al, 1967;Bariana, 1971;Holland et al, 1975). In recent years, our group has been engaged in the preparation of derivatives of 8-azaguanine via aza-Wittig reaction of beta-ethoxycarbonyl iminophosphorane with aromatic isocyanate (Zhao, Xie et al, 2005).…”

5-(4-Chlorophenoxy)-6-isopropyl-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one

“…For the biological activity of 8-azaguanine derivatives, see: Roblin et al (1945); Ding et al (2004); Mitchell et al (1950); Levine et al (1963); Montgomery et al (1962); Yamamoto et al (1967); Bariana (1971); Holland et al (1975); For related structures, see: Ferguson et al (1998); Li et al (2004); Zhao, Xie et al (2005); Zhao, Hu et al (2005); Zhao, Wang & Ding (2005); Chen & Shi (2006); Maldonado et al (2006); Xiao & Shi (2007); Wang et al (2006Wang et al ( , 2008; Zeng et al (2006Zeng et al ( , 2009.…”