5452-43-7

Usage

Structure

Pyrimidine derivative with a chloro group attached to the sixth carbon atom and a cyclopentyl group attached to the fourth and fifth nitrogen atoms in the pyrimidine ring

Uses

Commonly used in the pharmaceutical industry as a building block for the synthesis of drug candidates and other biologically active molecules

Value

Unique structure and chemical properties make it a valuable intermediate for the production of new chemical entities with potential therapeutic benefits

Applications

May have applications in other fields such as materials science and agrochemicals

InChI:InChI=1/C9H13ClN4/c10-8-7(11)9(13-5-12-8)14-6-3-1-2-4-6/h5-6H,1-4,11H2,(H,12,13,14)

Upstream product

• 5413-85-4 5-amino-4,6-dichloropyridimine 
• 1003-03-8 Cyclopentamine 
• 71-36-3 butan-1-ol 

Downstream Products

• 5444-81-5 6-chloro-9-cyclopentyl-9H-purine 

Relevant academic research and scientific papers

3,4-dichloroisothiazole heterocyclic purine derivatives as well as preparation method and application thereof

The invention provides a 3,4-dichloroisothiazole bipurine derivative as well as a preparation method and application thereof, and particularly relates to the 3,4-dichloroisothiazole bipurine derivative of which the chemical structural general formula is s

Design, Synthesis, and Evaluation of Novel Isothiazole-Purines as a Pyruvate Kinase-Based Fungicidal Lead Compound

Target identification is one of the most important bases for novel pesticide development; pyruvate kinase (PK) was discovered as a potent fungicide target in our previous studies. To continue the PK-based fungicide development, novel isothiazole-purine derivatives were rationally designed and synthesized. Bioassay results showed that compound 5ai displayed excellent in vitro activity against Rhizoctonia solani with an EC50 of 1.5 μg/mL, which was superior to those of positive controls diflumetorim with its EC50 of 19.8 μg/mL and PK-based lead YZK-C22 with its EC50 of 4.2 μg/mL. Compounds 3b (5.2 μg/mL) and 3c (4.5 μg/mL) displayed better activities against Gibberella zeae with their EC50s falling between 4.0 and 5.5 μg/mL, while YZK-C22 showed an EC50 of 6.4 μg/mL. In addition, 5ah exhibited promising in vivo activity against Erysiphe graminis and Puccinia sorghi Schw. with 100% efficacy at 10 μg/mL and 90% efficacy at 2 μg/mL against P. sorghi Schw. Compound 5ai showed good PK inhibitory activity with an IC50 of 38.8 μmol/L, and it was well docked into the active site of the target enzyme PK, which was slightly more active than YZK-C22 with its IC50 of 42.4 μmol/L. Our studies discovered that isothiazole-purines were PK-based fungicidal leads deserving of further study.

6-(alkylamino)-9-alkylpurines. A new class of potential antipsychotic agents

A series of 6-(alkylamino)-9-alkylpurines was synthesized and evaluated for the property of antagonizing the behavioral effects in animals of the dopamine agonist apomorphine. This model for identifying potential antipsychotic agents is based on the hypothesis that agents that antagonize apomorphine-induced aggressive behavior in rats and apomorphine-induced climbing in mice, but that do not block stereotyped behavior, could have an antipsychotic effect in humans without producing extrapyramidal side effects. The antiaggressive-behavior activity of lead compound 1 (6-(dimethylamino)- 9-(3-phenylalaninamidobenzyl)-9H-purine) was improved 48-fold with 6- (cyclopropylamino)-9-(cyclopropylmethyl)-2-(trifluoromethyl)-9H-purine (80) (po ED50 of 2 mg/kg), which was obtained through an iterative sequence of structure-activity relationship studies that encompassed evaluation of the effects of structure variations at the purine 9-, 6-, and 2-positions. Potency was enhanced with a 9-cyclopropyl group, the duration of action was improved with the 6-(cyclopropylamino) substituent, potency was further enhanced with an N-formyl prodrug, and an agent with reduced cardiovascular effect emerged with the 2-trifluoromethyl purine 80. This potential antipsychotic agent was not developed further due to undesirable effects on the stomach.

Antiparasitic 3(4-amino benzotriazo-1-yl-)1,2-cyclopentanediols

The present invention relates to the use of a compound of formula (I) STR1 wherein R represents a hydrogen atom; a C1-4 alkyl group; a group COR1 wherein R1 represents amino or C1-4 alkoxy; or a group --CH2 R2 wherein R2 represents a halogen atom (e.g. chlorine or bromine), C1-4 alkylthio, or azido, X and Y each independently represent --CH-- or --N; and Z represents --CR3, wherein R3 is hydrogen or C1-4 alkyl, or Z represents --N--; or a physiologically acceptable salt, ester or other physiologically functional derivative thereof, for the manufacture of a medicament for the treatment and/or prophylaxis of a parasitic infection in a mammal, and to certain novel compounds of formula (I), pharmaceutical compositions containing them and processes for their preparation.