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Several catalyzed alkylation reactions of 9-methyladenine by a model [CPI, cyclopropa[c]pyrrolo-[3,2-e]indol-4(5H)-one] 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. The effect on the CPI reactivity induced by water, formic and phosphoric acids (general acid catalysis), H3O+ (specific acid catalysis), sodium, and ammonium cation complexation (cationic catalysis) has been investigated.

Modeling Acid and Cationic Catalysis on the Reactivity of Duocarmycins

FRECCERO, MAURO
;GANDOLFI, REMO
2005-01-01

Abstract

Several catalyzed alkylation reactions of 9-methyladenine by a model [CPI, cyclopropa[c]pyrrolo-[3,2-e]indol-4(5H)-one] 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. The effect on the CPI reactivity induced by water, formic and phosphoric acids (general acid catalysis), H3O+ (specific acid catalysis), sodium, and ammonium cation complexation (cationic catalysis) has been investigated.
2005
The Organic Chemistry/Polymer Science category includes resources concerned with the related fields of organic chemistry and polymer science. The organic chemistry resources deal with compounds of carbon with the exception of certain simple ones, such as the carbon oxides, carbonates, cyanides and cyanates (see Inorganic & Nuclear Chemistry). This category includes research on synthetic and natural organic compounds that may include other elements, such as hydrogen and oxygen, but also nitrogen, halogens, sulphur and phosphorous. Resources concerned with hydrocarbons, organic compounds containing only the elements carbon and hydrogen, are also included in this category. Examples are the alkanes, alkenes, alkynes and aromatics, such as benzene and naphthalene. Polymer science includes all resources dealing with the study, production and technology of polymers, which are compounds composed of very large molecules made up of repeating molecular units (monomers). Polymers may be natural substances, such as polysaccharides or proteins, or synthetic materials, such as nylon or polyethylene.
JOURNAL OF ORGANIC CHEMISTRY
sì
WOS:000231573200010
2-s2.0-24144492999
Esperti anonimi
Inglese
Internazionale
STAMPA
70
7098
7106
9
Duocarmycins; cyclopropylpyrroloindoles; Acid Catalysis
2
info:eu-repo/semantics/article
262
Freccero, Mauro; Gandolfi, Remo
1 Contributo su Rivista::1.1 Articolo in rivista
none
1.1 Articolo in rivista
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11571/132142
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