An efficient total synthesis of 3′-azido-3′-deoxythymidine (AZT) and 3′-azido-2′,3′-dideoxyuridine (AZDDU, CS-87) from D-mannitol

Chu, Chung K.; Beach, Joseph Warren; Ullas, G. V.; Kosugi, Yoshiyuki

doi:10.1016/s0040-4039(00)82864-6

Cited by 58 publications

(15 citation statements)

References 17 publications

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“…Found: C,52.92;H,6.90;N,methyl]-3 '-deoxythymidine (36). A solution of 35 (Chu et al, 1988) (0.20 g, 0.53 mmol) in dry acetone (6 ml) was added dry K 2 CO 3 (0.08 g, 0.60 mmol) and methylbromoacetate (0.10 ml, 1.1 mmol). The reaction mixture was refluxed for 5 h and then concentrated to dryness.…”

Section: ' 5 ' -B I S -O -( T E R T -B U T Y L D I M E T H Y L S I mentioning

confidence: 99%

Structure-Activity Relationship Studies on a Novel Family of Specific HIV-1 Reverse Transcriptase Inhibitors

Bonache

Chamorro

Lobatón

et al. 2003

Antivir Chem Chemother

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We have previously reported the discovery and preliminary structure-activity relationships of a new class of specific HIV-1 reverse transcriptase (RT) inhibitors whose prototype compound is the 1-[2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3-N-[(carboxy) methyl]-thymine. In an attempt to increase the inhibitory efficacy against HIV-1 RT of this new class of nucleosides, and to further explore the structural features required for anti-HIV-1 activity, different types of modifications have been carried out on the prototype compound. These include substitution of the tert-butyldimethylsilyl groups by other liphophilic groups, replacement of the carboxy group at the N-3 position of the nucleobase by other functional groups, change in the length of the spacer between the thymine and the carboxylic acid residue and substitution of the thymine moiety by other pyrimidine (uracil, 5-ethyluracil) or purine (hypoxanthine) nucleobases. In addition, the most salient structural features of this new class of HIV-1-specific nucleosides have been incorporated into classical HIV RT nucleoside inhibitors such as ddl, AZT, d4T. Our studies demonstrate that both the carboxymethyl moiety at the nucleobase and tert-butyldimethylsilyl groups at the sugar are important structural components since deletion of either of them is detrimental to the antiviral activity.

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Section: ' 5 ' -B I S -O -( T E R T -B U T Y L D I M E T H Y L S I mentioning

confidence: 99%

Structure-Activity Relationship Studies on a Novel Family of Specific HIV-1 Reverse Transcriptase Inhibitors

Bonache

Chamorro

Lobatón

et al. 2003

Antivir Chem Chemother

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“…Similarly, pyrimidine and its derivatives have a unique place and have contributed significantly to biological and medicinal fields [25] such as antitubercular [26], calcium channel blockers [27] and also many pyrimidines have displayed diverse pharmaceutical activities [28] depending upon the geometry and type of substituents attached to the ring [29]. 3-Azido-3-deoxythymidine (AZT) [30] a pyrimidine derivative has been found to be a potent antiviral agent against HIV type 1 in vitro and has found to decrease mortality and opportunistic infections in patients with AIDS.…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Bis-pyrimidines Linked with Thiazolidin-4-one as New Antibacterial Agents

et al. 2019

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A series of novel 3-4-[2-hydroxy-5-(4-hydroxy-3-2-[2-(aryl)-4-oxo-1,3-thiazolan-3-yl]-6-phenyl-4-pyrimidinylbenzyl)phenyl]-6-phenyl-2-pyrimidinyl-2-(aryl)-1,3-thiazolan-4-ones 5(a-j) have been synthesized and assayed for their antibacterial activity against B. subtilis, B. sphaericus, S. aureus, P. aeruginosa, K. Aerogenes and C. violaceum. The inhibition zones and minimal inhibitory concentrations were measured and compared with the streptomycin. The antibacterial screening data reveal that the compounds containing 4-nitrophenyl (5c), 3-nitrophenyl (5d), 4-dimethylaminophenyl (5g) and 1,3-benzodioxole (5j) moiety at 2-position of the thiazolidin-4-one ring exhibited potent inhibitory activity towards all the tested microorganism, which is higher than streptomycin. The other compounds also showed moderate to good activity.

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“…3-Azido-3-deoxythymidine (AZT) [24] a pyrimidine derivative has been found to be a potent antiviral agent against HIV type 1 in vitro, and has been found to decrease mortality and opportunistic infections in patients with AIDS. Inspired by the biological profile of thiazolidinones and pyrimidine derivatives and their increasing importance in pharmaceutical and biological fields, and in continuation of our work on the synthesis of biologically active heterocycles [25] considering the scope to introduce pyrimidinyl moiety into thiazolidinones, it was thought 1122 A. Srinivas, A. Nagaraj and Ch.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some novel methylene‐bis‐pyrimidinyl‐spiro‐4‐thiazolidinones as biologically potent agents

Srinivas

Nagaraj

Reddy

2008

Journal of Heterocyclic Chem

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A series of novel methylene‐bis‐pyrimidinyl‐spiro‐4‐thiazolidinones 6a‐h have been synthesized by cyclocondensation of thioglycolic acid with methylene‐bis‐(N‐cyclohexylidene‐N‐pyrimidine) 5a‐h, which in turn have been prepared by the reaction of cyclohexanone with methylene‐bis‐2‐aminopyrimidines 4a‐h, which are prepared by the reaction of guanidine hydrochloride with methylene‐bis‐chalcones 3a‐h. The compounds 3a‐h have been synthesized by the reaction of 5‐(3‐formyl‐4‐hydroxybenzyl)‐2‐hydroxybenzaldehyde 2 with various acetophenones in presence of KOH. The compound 2 is prepared by the reported method. The structures of the compounds synthesized have been confirmed by their elemental analysis and spectral data. Their antibacterial and antifungal activities have also been evaluated.

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An efficient total synthesis of 3′-azido-3′-deoxythymidine (AZT) and 3′-azido-2′,3′-dideoxyuridine (AZDDU, CS-87) from D-mannitol

Cited by 58 publications

References 17 publications

Structure-Activity Relationship Studies on a Novel Family of Specific HIV-1 Reverse Transcriptase Inhibitors

Structure-Activity Relationship Studies on a Novel Family of Specific HIV-1 Reverse Transcriptase Inhibitors

Design and Synthesis of Bis-pyrimidines Linked with Thiazolidin-4-one as New Antibacterial Agents

Synthesis of some novel methylene‐bis‐pyrimidinyl‐spiro‐4‐thiazolidinones as biologically potent agents

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