Synthesis and anticancer activity of thiosubstituted purines

Kowalska, Alicja; Latocha, Małgorzata; Pluta, Krystian

doi:10.1007/s00044-015-1364-2

Cited by 13 publications

(10 citation statements)

References 30 publications

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“…2-Chloro-6-(prop-2-ynylthio)-7-methylpurine 1 was obtained via S-alkylation of the appropriate 6-purinethione with propargyl bromide (as solution in toluene) in DMF at room temperature in the presence of potassium tert -butoxide (Kowalska et al 2015 ). Using this procedure, 2,6-dipropynylthio-7-methylpurine 4 was obtained from 2,6-purinethione 3 .…”

Section: Resultsmentioning

confidence: 99%

“…2-Chloro-6-propynylthio-7-methylpurine 1 , (Kowalska et al 2015 ), 7-methylpurine-2,6-dithione 3 (Kowalska 2007 ), and 2,6-dichloro-7-methylpurine 11 (Kowalska et al 1985 ) were obtained according to the previously described method. Theobromine was commercially available from Sigma-Aldrich.…”

Section: Methodsmentioning

confidence: 99%

“…8-(Prop-2-ynylthio)-3,7-dimethylxanthine 9 was obtained from xanthine-8-thione 8 (0.11 g, 0.5 mmol) with propargyl bromide in DMF according to the previously described procedure (Kowalska et al 2015 ).…”

Section: Methodsmentioning

confidence: 99%

“…8-(Aminobut-2-ynylthio)-3,7-dimethylxanthines 10a-d were obtained from 8-propynylthio derivative 9 (0.125 g, 0.5 mmol) and appropriate amines (pyrrolidine, piperidine, morpholine, and diethylamine, 0.7 mmol) in dry dioxane according to the described procedure (Kowalska et al 2015 ).…”

Section: Methodsmentioning

confidence: 99%

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Synthesis and anticancer activity of multisubstituted purines and xanthines with one or two propynylthio and aminobutynylthio groups

2018

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A synthesis of new 2,6-disubstituted and 2,6,8-trisubstituted 7-methylpurines as well as 8-substituted 3,7-dimethylxanthines containing a triple bond chain have been worked out. Purinethiones and xanthinethiones were converted into propynylthio derivatives, which were then further transformed via a Mannich reaction into aminobutynylthio derivatives (amine = pyrrolidine, piperidine, morpholine, and diethylamine). The products thus obtained represent various types of the purine and xanthine structure: 8-mono-, 2,6- and 6,8-dipropynylthio, 6- and 8-monoaminobutynylthio, 2,6- and 6,8-diaminobutynylthio derivatives. All of these compounds were tested for their anticancer activity against human glioblastoma SNB-19, human adenocarcinoma MDA-MB-231, and melanoma C-32 cell lines. The anticancer activity depends on the nature of the substituent and its localization in the purine and xanthine framework. Generally, compounds possessing two alkynylthio groups (propynylthio or aminobutynylthio) were more active than those possessing only one group. Some compounds exhibited stronger or similar anticancer activity to cisplatin. All compounds were also tested for their cytotoxic activity against normal human fibroblasts (HFF-1). The most promising anticancer compounds were found to be 2,6-dipropynylthio-7-methylpurine 4, 2-chloro-6,8-dipropynylthio-7-methylpurine 14, and 2-chloro-6,8-di(N-morpholinylbutynylthio)-7-methylpurine 15c acting selectively on glioblastoma SNB-19, melanoma C-32, and adenocarcinoma MDA-MB-231 with the IC50 = 0.07–4.08 μg/mL.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Synthesis and anticancer activity of multisubstituted purines and xanthines with one or two propynylthio and aminobutynylthio groups

2018

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“…Several purine-derivatives have been considered as important and effective drugs used in cancer chemotherapy, for immunosuppression in kidney or heart transplantation and autoimmune diseases [184,185]. Various pharmacological effects of such compounds including antiviral, antibacterial, antitumor, and antifungal activity were developed for treatment of patients suffering different illness [186]. For this reason, many thiopurine derivatives and analogs have been synthesized for evaluation of their biological activities and reduced toxicity.…”

Section: Purine-like Pyrrolo[23-d]pyrimidine Systems Of Anticancer Imentioning

confidence: 99%

Synthesis of Biologically Active Molecules through Multicomponent Reactions

et al. 2020

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Focusing on the literature progress since 2002, the present review explores the highly significant role that multicomponent reactions (MCRs) have played as a very important tool for expedite synthesis of a vast number of organic molecules, but also, highlights the fact that many of such molecules are biologically active or at least have been submitted to any biological screen. The selected papers covered in this review must meet two mandatory requirements: (1) the reported products should be obtained via a multicomponent reaction; (2) the reported products should be biologically actives or at least tested for any biological property. Given the diversity of synthetic approaches utilized in MCRs, the highly diverse nature of the biological activities evaluated for the synthesized compounds, and considering their huge structural variability, much of the reported data are organized into concise schemes and tables to facilitate comparison, and to underscore the key points of this review.Molecules 2020, 25, 505 2 of 71 acetylcholinesterase inhibitors, anti-HIV, antimicrobial, antioxidant, anti-mycobacterial and anticancer activities ( Figure 1). It is noteworthy that 64% and 16% of the supporting literature found for this review correspond to heterocyclic structures with anticancer and antimicrobial activities, respectively. Scheme 2. Three-component synthesis of 3,4-dihydropyrimidinones/thiones type 7 under microwave irradiation, for anti-inflammatory activity.Patil et al., reported a one-pot pseudo-five-component synthesis of highly functionalized tetrahydropyridines 9 using Cu(OTf) 2 as catalyst, Scheme 3. In vitro anti-inflammatory activity of the obtained compounds 9 was determined against matrix metalloproteinases (MMPs) as MMP-2 and MMP-9 by using gelatin zymography [29]. Scheme 3. Multicomponent Cu(OTf) 2 catalyzed synthesis of substituted tetrahydropyridines 9 for anti-inflammatory activity.A highly diastereoselective synthesis (exclusively the cis isomer is formed), of chromeno β-lactam hybrids 13/14 was also achieved by an efficient one-pot three-component reaction between either 5,5-dimethylcyclohexane-1,3-dione (10a) or 4-hydroxycoumarin (10b), diverse benzaldehydes 11 and malononitrile (12), in the presence of DABCO under reflux conditions (Scheme 4). Scheme 4. Three-component synthesis of β-lactam hybrids 13/14 for anti-inflammatory activity.The synthesized compounds (13 in 80-95% yield) and (14 in 82-95% yield) were screened for anti-inflammatory activity (as well as for anticancer activity, please see Section 3.13.13. Compound 13b (Ar = 4-ClC 6 H 4 , Ar 1 = 4-MeC 6 H 4 ) was the most active of all the chromeno β-lactam hybrids 13/14 tested, with a 19.8 anti-inflammatory ratio, although, it resulted less active than the reference drug dexamethasone corticosteroid used for the treatment of rheumatoid and skin inflammation [30].

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Efficient synthetic strategies for fused pyrimidine and pyridine derivatives: A review

Anjirwala,

Patel

2024

Journal of Heterocyclic Chem

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Pyrimidine and its derivatives play a paramount role in drug discovery as privileged pharmacophores with considerable chemical and biological significance and its presence in genes. This review aims to assemble a systematic evaluation of synthetic tactics of various fused pyrimidine derivatives containing nitrogen heterocycles such as pyridopyridines, pyridopyrimidines, and pyrimidopyrimidine from a pharmacological point of view and deliver an overview of methodologies presenting the chemistry of fused pyrimidine derivatives. The review details the importance of various catalysts and ring substitution using various electrophilic and nucleophilic reagents. These synthetic strategies were elaborated based on the different synthetic routes that lead to the specific type of pyrimidine and pyridine fused derivatives. The literature accumulates various developments in one‐pot condensation, the Knoevenagel–Michael addition mechanism, microwave and ultrasound irradiation, intramolecular cyclization, nano‐catalytic reactions, and so forth. Short reaction times, catalyst reusability, solvent‐free conditions, excellent yields, and stereo‐selectivity are some of the benefits of certain synthetic approaches.

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Synthesis and anticancer activity of thiosubstituted purines

Cited by 13 publications

References 30 publications

Synthesis and anticancer activity of multisubstituted purines and xanthines with one or two propynylthio and aminobutynylthio groups

Synthesis and anticancer activity of multisubstituted purines and xanthines with one or two propynylthio and aminobutynylthio groups

Synthesis of Biologically Active Molecules through Multicomponent Reactions

Efficient synthetic strategies for fused pyrimidine and pyridine derivatives: A review

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