A facile and rapid one-step synthesis of 8-substituted xanthine derivatives via tandem ring closure at room temperature

Bandyopadhyay, Prabal; Agrawal, Sumit K.; Sathe, Manisha; Sharma, Pratibha; Kaushik, M. P.

doi:10.1016/j.tet.2012.03.050

Cited by 28 publications

(16 citation statements)

References 43 publications

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“…In spite of broader pharmaceutical applications and similarity to purine family, xanthine‐based research has not taken up full measure thus limiting synthesis of xanthine‐based molecules (Monteiro et al, 2016). The most noticeable reason for this is adverse synthetic procedures such as ring closure and condensation method for the production of new products (Allwood et al, 2007; Bandyopadhyay et al, 2012; Chen et al, 2014; Hayallah et al, 2002; Kim et al, 2010; Lee et al, 2016; Sakai et al, 1992;). In terms of xanthine‐based drug development, large scale synthesis is not supported thus there is crucial need for the development of feasible synthetic methods so that new xanthine‐based drug candidates can be introduced.…”

Section: Introductionmentioning

confidence: 99%

Bronchospasmolytic activity and adenosine receptor binding of some newer 1,3‐dipropyl‐8‐phenyl substituted xanthine derivatives

Gumber

Yadav

et al. 2020

Chem Biol Drug Des

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The aldehyde derivatives of 1,3-dipropyl xanthines as described in this paper, constitutes a new series of selective adenosine ligands displaying bronchospasmolytic activity. The effect of substitution at third-and fourth-position of 8-phenyl xanthine has also been taken into consideration. The synthesized compounds showed varying binding affinities at different adenosine receptor subtypes (A 1 , A 2A , A 2B , and A 3 ) and also good in vivo bronchospasmolytic activity against histamine aerosol-induced asthma in guinea pigs. Most of the compounds showed maximum affinity toward the A 2A receptor subtype. The monosubstituted 3-aminoalkoxyl 8-phenyl xanthine with a aminodiethyl moiety (compound 12e) was found to be most potent A 2A adenosine receptor ligand (K i = 0.036 µM) followed by disubstituted 4-aminoalkoxyl-3-methoxy-8-phenyl xanthine (K i = 0.050 µM) (compound 10a). K E Y W O R D Sadenosine, antiasthmatics, bronchospasmolytic, radioligand binding, xanthines

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Section: Introductionmentioning

confidence: 99%

Bronchospasmolytic activity and adenosine receptor binding of some newer 1,3‐dipropyl‐8‐phenyl substituted xanthine derivatives

Gumber

Yadav

et al. 2020

Chem Biol Drug Des

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“…при лікуванні астми, бронхіту і хронічної об структивної хвороби легень. Також похідні ксантину знайшли застосування як ді уретики, аналгетики, серцеві стимулятори, протизапальні, психотропні й ниркові за хисні агенти [2][3][4][5].…”

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“…Масспектр 1бензил8тіотеоброміну (2) (m/z 1%): 303 (21,6), 302 (93,3), 301 (31,5), 285 (6,5), 211 (20,0), 210 (6,0), 197 (5,8), 169 (7,3), 168 (7,0), 152 (20,5), 149 (6,3), 141 (6,0), 132 (7,2), 111 (38,7), 110 (11,2), 99 (22,9), 98 (9,3), 92 (6,7), 91 (99, 9), 90 (30,2), 85 (5,5), 83 (10,5), 82 (9,9), 81 (6,4), 77 (8,6), 70 (20,4), 69 (12,2), 67 (16,4), 65 (14, 9), 55 (7,2), 43 (11,5), 42 (11,6), 41 (8,7). (3)(4)(5)(6)(7)(8). Суміш 5 ммоль 1бензил8 тіотеоброміну (2), 6 ммоль відповідного галогенкетону чи хлороацетаміду, 20 мл води, 20 мл етанолу кип'ятять 20 хв, охолоджують, осад, що утворився, відфільтро вують, промивають водою (3,4), водним ізопропіловим спиртом (5-8) та перекриста лізовують із водного ізопропілового спирту (3,4), чи водного діоксану (5)(6)(7)(8).…”

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“…(3)(4)(5)(6)(7)(8). Суміш 5 ммоль 1бензил8 тіотеоброміну (2), 6 ммоль відповідного галогенкетону чи хлороацетаміду, 20 мл води, 20 мл етанолу кип'ятять 20 хв, охолоджують, осад, що утворився, відфільтро вують, промивають водою (3,4), водним ізопропіловим спиртом (5-8) та перекриста лізовують із водного ізопропілового спирту (3,4), чи водного діоксану (5)(6)(7)(8).…”

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Synthesis, physical-chemical and biological properties of 8-R-thioderivatives of 1-benzyltheobromine

Иванченко

Романенко

Samura

et al. 2018

Farm Zh

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Key way for creating new medicinal drugs is structural modification of known and existent natural compounds with high biological activity. In this aspect researchers’ attention is drawn by xanthine derivatives which appear to be antagonists of adenosine receptors, phosphodiesterase inhibitors and histone deacetylase inducers. This resulted in their widespread application in medicine to cure asthma, bronchitis and chronic obstructive pulmonary disease. In addition, xanthine derivatives are used as diuretics, analgesics, heart pacemakers, anti-inflammatory, psychotropic and renal protective agents. The aim of this work lies in developing unique methods to synthesize undocumented in other scientific papers 8-thioderivatives of 1-benzylthiobromine and also studying of their physical, chemical and biological properties. Acute toxicity of synthesized compounds has been studied with the application of Kerber method. The study of diuretic activity of obtained compounds was carried out applying Berkhin method. Analgesic activity of synthesized xanthines was studied at ‘acetic acid writhing’ model. Anti-inflammatory activity was studied at ‘acute aseptic edema’ model. Antioxidant activity was studied in vitro using the method of non-enzymatic initiation of free-radical oxidation. Heating of 1-benzyl-8-bromotheobromine with double excess of sodium sulphidenonahydrate in dimethylformamide environment results in formation of 8-thiotheobromine. Reactions of thioxanthines with halogenketones and chloroacetamide proceed smoothly with their short-time heating in aqueous alcohol environment. By applying such computer programs as ALOGPS, DRAGON, GUSAR and ACD/Percepta Platform was established viability of further invitro and invivo research. Accessible laboratory methods have been elaborated to synthesize 8-thiosubstituted 1-n-methylbenzyltheobromine, their structure having been proved by elemental analysis, PMR-spectroscopy and mass-spectrometry data. Molecular and pharmacological descriptors to forecast properties of the obtained substances have been calculated, in addition to acute toxicity index. Also the study of acute toxicity, diuretic, analgesic, anti-inflammatory and anti-oxidant activity of synthesized compounds has been carried out. After additional research 1-benzyl-8-(2-oxo-2-phenylethylthio)theobromine can be used in medical practice as an antioxidant agent.

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ChemInform Abstract: A Facile and Rapid One‐Step Synthesis of 8‐Substituted Xanthine Derivatives via Tandem Ring Closure at Room Temperature.

et al. 2012

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A Facile and Rapid One-Step Synthesis of 8-Substituted Xanthine Derivatives via Tandem Ring Closure at Room Temperature. -NBS efficiently promotes the condensation of aldehydes with uracil derivative (I) in the presence of a catalytic amount of AIBN in a single step via a radical chain reaction. -(BANDYOPADHYAY, P.; AGRAWAL, S. K.; SATHE, M.; SHARMA, P.; KAUSHIK*, M. P.; Tetrahedron 68 (2012) 20, 3822-3827, http://dx.

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A facile and rapid one-step synthesis of 8-substituted xanthine derivatives via tandem ring closure at room temperature

Cited by 28 publications

References 43 publications

Bronchospasmolytic activity and adenosine receptor binding of some newer 1,3‐dipropyl‐8‐phenyl substituted xanthine derivatives

Bronchospasmolytic activity and adenosine receptor binding of some newer 1,3‐dipropyl‐8‐phenyl substituted xanthine derivatives

Synthesis, physical-chemical and biological properties of 8-R-thioderivatives of 1-benzyltheobromine

ChemInform Abstract: A Facile and Rapid One‐Step Synthesis of 8‐Substituted Xanthine Derivatives via Tandem Ring Closure at Room Temperature.

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