4551-95-5Relevant articles and documents
Pyrimidinethione-containing purine compound and application thereof
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Paragraph 0018-0020; 0022, (2020/01/25)
The invention discloses a pyrimidinethione-containing purine compound having a structure represented by a formula I shown in the specification and an application of the compound as a plant growth regulator. The compound represented by the formula I has excellent cell division activity and plant growth regulating activity of promoting rooting, increasing the yield and improving the quality, and canbe widely used for rooting, seedling strengthening, yield increasing and quality improvement of crops such as grain, cotton, fruits and vegetables or plants through the manners of treating seeds, being sprayed to roots and stem leaves, at the same time, the compound represented by the formula I has a bactericidal effect, and the characteristics of safe use, low costs, and significant effects.
A Study on the Intramolecular Mitsunobu Reaction of N6-(ω-Hydroxyalkyl)adenines
?im?nková, Nadě?da,Tobrman, Tomá?,Eigner, Václav,Dvo?ák, Dalimil
, p. 3565 - 3573 (2017/11/21)
The cyclization of N6-(ω-hydroxyalkyl)adenines with a N6H-group leads to N6,N1 ring closure regardless of the method of the cyclization that was used. Five-membered to eight-membered rings were obtained using NBS/PPh3; however, under Mitsunobu conditions, the eight-membered fused purine was not formed. Surprisingly, the cyclization of N6-methyl-N6-(4-hydroxybutyl)adenine only leads to N6,N7 ring closure using both methods.
Synthesis and cytostatic activity of N-[2-(phosphonomethoxy)alkyl] derivatives of N6-substituted adenines, 2,6-diaminopurines and related compounds
Holy, Antonin,Votruba, Ivan,Tloustova, Eva,Masojidkova, Milena
, p. 1545 - 1592 (2007/10/03)
N6-Substituted adenine and 2,6-diaminopurine derivatives of 9-[2-(phosphonomethoxy)ethyl] (PME), 9-[(R)-2-(phosphonomethoxy)propyl] [(R)-PMP] and enantiomeric (S)-PMP series were synthesized by reactions of primary or secondary amines with 6-chloro-9-{[2-(diisopropoxyphosphoryl)methoxy]alkyl}purines (26-28) or 2-amino-6-chloro-9-{[2-(diisopropoxyphosphoryl)methoxy]alkyl}purines (29-31) followed by treatment of the diester intermediates 32 with bromo(trimethyl)silane and hydrolysis. Diesters 32 were also obtained by reaction of N6-substituted purines with synthons 23-25 bearing diisopropoxyphosphoryl group. Alkylation of 2-amino-6-chloropurine (9) with diethyl [2-(2-chloroethoxy)ethyl]phosphonate (148) gave the diester 149 which was analogously converted to N6-substituted 2,6-diamino-9-[2-(2-phosphonoethoxy)ethyl]purines 151-153. Alkylation of N6-substituted 2,6-diaminopurines with (R)-[(trityloxy)methyl]oxirane (155) followed by reaction of thus-obtained intermediates 156 with dimethylformamide dimethylacetal and condensation with diisopropyl [(tosyloxy)methyl]phosphonate (158) followed by deprotection of the intermediates 159 gave N6-substituted 2,6-diamino-9-[(S)-3-hydroxy-2-(phosphononiethoxy)propyl]purines 160-163. The highest cytostatic activity in vitro was exhibited by the following N6-derivatives of 2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine (PMEDAP): 2,2,2-trifluoroethyl (53), allyl (54), [(2-dimethylamino)ethyl] (68), cyclopropyl (75) and dimethyl (91). In CCRF-CEM cells, the cyclopropyl derivative 75 is deaminated to the guanine derivative PMEG (3) which is then converted to its diphosphate.