POTENTIAL ANTICANCER AGENTS.<sup>1</sup> XL. SYNTHESIS OF THE β-ANOMER OF 9-(D-ARABINOFURANOSYL)-ADENINE

Lee, William W.; Benitez, Allen; Goodman, Leon; Baker, B. R.

doi:10.1021/ja01495a070

Cited by 172 publications

(47 citation statements)

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“…Perhaps the best examples for this comment are two very early drugs in this section, vidarabine (72) and acyclovir (73). In the first case, the change of the sugar to arabinose (as mentioned earlier, this was coincidental with the reports of the Bergmann group, though whether Lee et al, 34 had prior knowledge is unknown), yielded a compound that was designed to be an antitumor agent but gained fame as an anti-herpes simplex drug. Similarly, perhaps the most "famous" of these early nucleosides was azidothymidine (AZT; 74).…”

Section: Antiviral Agents Based On Nucleosidesmentioning

confidence: 58%

“…In a review in 1991, Suckling 33 demonstrated how such structures evolved in the Wellcome laboratories, leading ultimately to molecules such as azidothymidine (74) or 34 reported the synthesis of arabinosyladenine (Ara-A or vidarabine, 72) as a potential antitumor agent, with a later report showing production by fermentation of S. antibioticus. 35 Then it was isolated and purified from the Mediterranean gorgonian Eunicella cavolini by the Cimino et al 36 in 1984.…”

Section: Drugs Derived From Nucleosidesmentioning

confidence: 99%

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Natural Product-Derived Drugs Based on β-Adrenergic Agents and Nucleosides

Newman¹

2016

Journal of the Brazilian Chemical Society

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This relatively short review demonstrates the very important role of the structures of the natural products adrenaline and relatives, in the design and subsequent approval of β-agonists and antagonists, and of modified nucleosides as anticancer, and in particular, antiviral agents against herpes (HSV), human immunodeficiency virus (HIV) and hepatitis C virus (HCV) that would not have been synthesized in the absence of knowledge of bioactive arabinose nucleosides.

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Section: Antiviral Agents Based On Nucleosidesmentioning

confidence: 58%

Section: Drugs Derived From Nucleosidesmentioning

confidence: 99%

Natural Product-Derived Drugs Based on β-Adrenergic Agents and Nucleosides

Newman¹

2016

Journal of the Brazilian Chemical Society

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“…40,41 Ara-C (4) é usada principalmente na terapia da leucemia aguda não linfoblástica, enquanto que ara-A (3) é utilizada 42 De acordo com Newman e Cragg, 10 o grande impacto da descoberta dessas moléculas foi demonstrar, pela primeira vez, a ocorrência de nucleosídeos naturais bioativos contendo açúcares diferentes da ribose e da deoxirribose. Pode-se dizer ainda que essa constatação deu origem a toda uma geração de nucleosídeos incomuns e não naturais com potencial terapêutico, incluindo o fármaco anti-HIV, azidotimidina ou AZT.…”

Section: Ara-c (Citarabina ® ) E Ara-a(vidarabina ® )unclassified

Organismos marinhos como fonte de novos fármacos: histórico & perspectivas

Costa-Lotufo¹,

Wilke²,

Jimenez³

et al. 2009

Quím. Nova

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Recebido em 15/1/09; aceito em 11/3/09; publicado na web em 2/4/09 MARINE ORGANISMS AS A SOURCE OF NEW PHARMACEUTICALS: HISTORY AND PERSPECTIVES. Though sharing only a short part on the natural products timeline, the studies on marine products has already handed in four new drugs to the clinical arsenal and brought up a long and promising list of unique molecules to pre-clinical and clinical trials. Thus, as the available analytical resources improve and the interest of large pharmaceutical companies arises, medical use of marine products has definitely become a reality.Keywords: marine biotechnology; natural products; marine drugs. intrOdUÇÃOOs produtos naturais têm sido a maior fonte de inspiração para diversas áreas da química e da ciência de um modo geral. Usando, copiando ou modificando as moléculas sintetizadas pelos seres vivos, o homem tem obtido inovações para o seu benefício em diversas áreas e, entre elas, a produção de fármacos. Do analgésico morfina, ao antibiótico penicilina, passando pelo anticâncer paclitaxel (Taxol ® ), estima-se que 80% dos fármacos em uso são produtos naturais ou foram inspirados pela natureza.Existem várias revisões recentes que podem ser consultadas para uma visão da contribuição dos produtos naturais na indústria farmacêutica. 1-4 Neste contexto, os organismos terrestres (principalmente micro-organismos e plantas) são os responsáveis por quase a totalidade dessas substâncias, enquanto que os organismos marinhos, apesar de promissores, passaram a ser investigados de maneira sistemática apenas recentemente. Nesta breve revisão comentaremos alguns aspectos históricos dos estudos químicos e farmacológicos realizados com organismos marinhos e suas implicações científicas, como a descoberta de novos produtos naturais com ação em alvos moleculares peculiares, além da utilização desse conhecimento pela indústria farmacêutica no processo de pesquisa e desenvolvimento (P&D) de fármacos.históricO Mares e oceanos ocupam mais de 2/3 da superfície da Terra e abrigam quase todos os grupos de organismos vivos, incluindo representantes de 34 dentre os 36 filos descritos. Sendo assim, os ecossistemas marinhos podem ser considerados como detentores da maior biodiversidade filética, com potencial biotecnológico associado praticamente ilimitado. [5][6][7][8] Até os anos 50, este ecossistema escapou do interesse dos cientistas de produtos naturais, principalmente devido ao difícil acesso às suas profundidades. Com o avanço das técnicas e o advento dos equipamentos seguros de mergulho, na década de 70, algas e invertebrados marinhos puderam dar início às suas histórias nas bancadas dos laboratórios de química e farmacologia. 7 O pesquisador Werner Bergmann da Universidade de Yale (E.U.A.) foi um dos pioneiros, na década de 50, no estudo dos produtos naturais marinhos. Um dos exemplos históricos no desenvolvimento de fármacos marinhos teve origem no seu trabalho de isolamento dos nucleosídeos espongouridina (1) e espongotimidina (2) da esponja Tethya crypta (Cryptotethya crypta). 9 Análogos sintét...

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“…The synthesis (9,26) and biological inhibitory activity (27, 28) of 9-P-D-arabinofuranosyiadenine (araA) were reported several years before its isolation from microbiological culture fermentation (29) and evaluation as a promising antiviral drug (30). Synthetic 9-P-D-xylofuranosyladenine (xyloA) (46, 31) was also shown to exhibit inhibitory activity against neoplastic cells (32).…”

Section: -8-pivalyl-p-d-xylofuranosyl)pyrrolo[23 -D L -mentioning

confidence: 99%

Nucleic acid related compounds. 25. Syntheses of arabino, xylo, and lyxo-anhydro sugar nucleosides from tubercidin ribo-epoxide

Robins¹,

Fouron²,

Muhs³

1977

Can. J. Chem.

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. Can J. Chem. 55, 1260Chem. 55, (1977. Treatment of the trans iodohydrin acetate, 4-arnino-7-(3-iodo-3-deoxy-2-O-acetyl-5-0-[2,5,5-trimethyl-1,3-dioxolan-4-on-2-yl]-~-~-xylofuranosyl)pyrrolo[2,3-d]pyrimidine (2) with methanolic ammonia gave 2',3'-anhydrotubercidin (3) in 96% yield. N4,N4,05'-Tribenzoylation of 3 gave 4, which is stabilized against intramolecular cyclization. Treatment of 4 with boron trifluoride etherate (3',5'-benzoxonium ion formation) followed by deblocking gave 4-amino-7-B-D-xylofuranosylpyrrolo[2,3-dlpyrimidine (5) in 91% overall yield from tubercidin (1). The 3',5'-0-isopropylidene derivative (6a) of 5 was mesylated to give 6b which was deprotected in acid and the resulting trans hydroxy mesylate was treated with base to give 4-amino-7-(2,3-anhydro-P-D-lyxofuranosyl)pyrrolo[2,3-d]rmdne (7

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POTENTIAL ANTICANCER AGENTS.¹ XL. SYNTHESIS OF THE β-ANOMER OF 9-(D-ARABINOFURANOSYL)-ADENINE

Abstract: COMMUNICATIONS TO THE EDITORVol. s2(V) bromide a t the temperature necessary for synthesis (ca. 100') keeps the yield very low and that

Cited by 172 publications

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Natural Product-Derived Drugs Based on β-Adrenergic Agents and Nucleosides

Natural Product-Derived Drugs Based on β-Adrenergic Agents and Nucleosides

Organismos marinhos como fonte de novos fármacos: histórico & perspectivas

Nucleic acid related compounds. 25. Syntheses of arabino, xylo, and lyxo-anhydro sugar nucleosides from tubercidin ribo-epoxide

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POTENTIAL ANTICANCER AGENTS.1 XL. SYNTHESIS OF THE β-ANOMER OF 9-(D-ARABINOFURANOSYL)-ADENINE

Abstract: COMMUNICATIONS TO THE EDITORVol. s2(V) bromide a t the temperature necessary for synthesis (ca. 100') keeps the yield very low and that

Cited by 172 publications

References 0 publications

Natural Product-Derived Drugs Based on β-Adrenergic Agents and Nucleosides

Natural Product-Derived Drugs Based on β-Adrenergic Agents and Nucleosides

Organismos marinhos como fonte de novos fármacos: histórico & perspectivas

Nucleic acid related compounds. 25. Syntheses of arabino, xylo, and lyxo-anhydro sugar nucleosides from tubercidin ribo-epoxide

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POTENTIAL ANTICANCER AGENTS.¹ XL. SYNTHESIS OF THE β-ANOMER OF 9-(D-ARABINOFURANOSYL)-ADENINE