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Chemical Compound Review

CHEMBL65976     9-methylpurin-6-amine

Synonyms: SureCN106573, NSC-7843, CCRIS 6905, AG-C-09394, AG-K-73882, ...
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High impact information on NAD

  • Several catalyzed alkylation reactions of 9-methyladenine by a model [CPI, cyclopropa[c]pyrrolo[3,2-e]indol-4(5H)-one (1)] of duocarmycin anticancer drugs have been compared to the uncatalyzed reaction in gas phase and in water solvent bulk, using density functional theory at the B3LYP level with the 6-31+G(d,p) basis set and C-PCM solvation model [1].
  • Stepwise migration of coordinated Pt(II) from the endocyclic N1 site to the exocyclic amino group occurs in the bis(9-methyladenine-N1) complex of cis-Pt(II)(NH(3))(2) in basic solution, whereafter deamination of the 9-methyladenine still coordinated at N-1 competes with a second migration step [2].
  • Hydrogen-bonding effects in the real crystalline structure of 9-methyladenine, 9-MA, were studied using calculated electric field gradient, EFG, and chemical shielding, CS, tensors for nitrogen and hydrogen nuclei via density functional theory [3].
  • A new antileukemic alkaloid, agelasine G (1a), has been isolated from the Okinawan marine sponge Agelas sp. and its structure elucidated to be a bromopyrrole alkaloid containing 9-methyladenine and diterpene moieties on the basis of the spectroscopic data [4].
  • Metabolic N-oxidation of adenine, 9-methyladenine, 9-benzyladenine, 9-benzhydryladenine and 9-trityladenine has been investigated using hepatic microsomes from hamster, guinea-pig, rabbit, mouse, rat, and dog [5].

Associations of NAD with other chemical compounds


Gene context of NAD

  • The experimental static deformation density of 9-methyladenine was obtained in a deformation refinement against the low-temperature X-ray data of Craven & Benci [Acta Cryst. (1981), B37, 1584-1591] [7].

Analytical, diagnostic and therapeutic context of NAD


  1. Modeling acid and cationic catalysis on the reactivity of duocarmycins. Freccero, M., Gandolfi, R. J. Org. Chem. (2005) [Pubmed]
  2. Platinum(II)-bis(9-methyladenine) complexes; N1-->N6 migration of Pt(II)vs deamination of coordinated methyladenine. Klika, K.D., Arpalahti, J. Chem. Commun. (Camb.) (2004) [Pubmed]
  3. An investigation of hydrogen-bonding effects on the nitrogen and hydrogen electric field gradient and chemical shielding tensors in the 9-methyladenine real crystalline structure: a density functional theory study. Mirzaei, M., Hadipour, N.L. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2006) [Pubmed]
  4. Agelasine G, a new antileukemic alkaloid from the Okinawan marine sponge Agelas sp. Ishida, K., Ishibashi, M., Shigemori, H., Sasaki, T., Kobayashi, J. Chem. Pharm. Bull. (1992) [Pubmed]
  5. Conformational analysis of 9-substituted adenines in relation to their microsomal N1-oxidation. Lam, S.P., Barlow, D.J., Gorrod, J.W. J. Pharm. Pharmacol. (1989) [Pubmed]
  6. Biological N-oxidation of adenine and 9-alkyl derivatives. Lam, S.P., Devinsky, F., Gorrod, J.W. European journal of drug metabolism and pharmacokinetics. (1987) [Pubmed]
  7. Static deformation densities for cytosine and adenine. Eisenstein, M. Acta Crystallogr., B (1988) [Pubmed]
  8. Structure and thermal vibrations of adenosine from neutron diffraction data at 123 K. Klooster, W.T., Ruble, J.R., Craven, B.M., McMullan, R.K. Acta Crystallogr., B (1991) [Pubmed]
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