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Literature DB >> 12459008

Discovery of 8-hydroxyadenines as a novel type of interferon inducer.

Kosaku Hirota¹, Kazunori Kazaoka, Itaru Niimoto, Hiroshi Kumihara, Hironao Sajiki, Yoshiaki Isobe, Haruo Takaku, Masanori Tobe, Haruhisa Ogita, Tetsuhiro Ogino, Shinji Ichii, Ayumu Kurimoto, Hajime Kawakami.

Abstract

9-Benzyl-8-hydroxyadenine (6) was found to possess interferon-inducing activity in vitro as a lead compound. Although replacement of the 9-benzyl group of 6 did not improve the activity, the introduction of a substituent such as alkyl, alkylthio, alkylamino, and alkoxy groups into the 2-position of the adenine ring resulted in a remarkable increase in the activity. The 2-alkylthio (30-32), 2-butylamino (41), and 2-butoxy (47) analogues indicated the highest activities by oral administration to mice.

Entities: Chemical Species

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Year: 2002 PMID： 12459008 DOI： 10.1021/jm0203581

Source DB: PubMed Journal: J Med Chem ISSN： 0022-2623 Impact factor: 7.446

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Cited

15 in total

1. Structure-activity relationships in human toll-like receptor 7-active imidazoquinoline analogues.

Authors: Nikunj M Shukla; Subbalakshmi S Malladi; Cole A Mutz; Rajalakshmi Balakrishna; Sunil A David
Journal: J Med Chem Date: 2010-06-10 Impact factor: 7.446

2. Optimization of 8-oxoadenines with toll-like-receptor 7 and 8 activity.

Authors: Hélène G Bazin; Laura S Bess; Mark T Livesay; Yufeng Li; Van Cybulski; Shannon M Miller; David A Johnson; Jay T Evans
Journal: Bioorg Med Chem Lett Date: 2020-01-22 Impact factor: 2.823

Review 3. Strategies for designing synthetic immune agonists.

Authors: Tom Y-H Wu
Journal: Immunology Date: 2016-07-11 Impact factor: 7.397

4. Pharmacokinetic-pharmacodynamic modeling of alpha interferon response induced by a Toll-like 7 receptor agonist in mice.

Authors: Neil Benson; Joost de Jongh; Jonathan D Duckworth; Hannah M Jones; Henry E Pertinez; Jaiessh K Rawal; Tamara J van Steeg; Piet H Van der Graaf
Journal: Antimicrob Agents Chemother Date: 2009-12-22 Impact factor: 5.191

5. Structural requirements for TLR7-selective signaling by 9-(4-piperidinylalkyl)-8-oxoadenine derivatives.

Authors: Hélène G Bazin; Yufeng Li; Juhienah K Khalaf; Sandra Mwakwari; Mark T Livesay; Jay T Evans; David A Johnson
Journal: Bioorg Med Chem Lett Date: 2015-01-31 Impact factor: 2.823

6. Facile syntheses of functionalized toll-like receptor 7 agonists.

Authors: Babatope Akinbobuyi; Matthew R Byrd; Charles A Chang; Mysa Nguyen; Zacharie J Seifert; Anne-Laure Flamar; Gerard Zurawski; Katherine C Upchurch; SangKon Oh; Stephen H Dempsey; Thomas J Enke; John Le; Hunter J Winstead; José R Boquín; Robert R Kane
Journal: Tetrahedron Lett Date: 2015-01-08 Impact factor: 2.415

Discovery of 8-hydroxyadenines as a novel type of interferon inducer.

1. Structure-activity relationships in human toll-like receptor 7-active imidazoquinoline analogues.

2. Optimization of 8-oxoadenines with toll-like-receptor 7 and 8 activity.

Review 3. Strategies for designing synthetic immune agonists.

4. Pharmacokinetic-pharmacodynamic modeling of alpha interferon response induced by a Toll-like 7 receptor agonist in mice.

5. Structural requirements for TLR7-selective signaling by 9-(4-piperidinylalkyl)-8-oxoadenine derivatives.

6. Facile syntheses of functionalized toll-like receptor 7 agonists.

7. Mast cell-dependent anorexia and hypothermia induced by mucosal activation of Toll-like receptor 7.

8. Structure-activity relationships in human Toll-like receptor 8-active 2,3-diamino-furo[2,3-c]pyridines.

9. 4-Hydrazinyl-1-isobutyl-1H-imidazo[4,5-c]quinoline.

Review 10. Structural evolution of toll-like receptor 7/8 agonists from imidazoquinolines to imidazoles.