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Molecular design and evaluation of aza-polycyclic carbamoyl pyridones as HIV-1 integrase strand transfer inhibitors.
Akiyama, Toshiyuki; Johns, Brian A; Taoda, Yoshiyuki; Yoshida, Hiroshi; Taishi, Teruhiko; Kawasuji, Takashi; Murai, Hitoshi; Yoshinaga, Tomokazu; Sato, Akihiko; Seki, Takahiro; Koyama, Mikiko; Miki, Shigeru; Kawauchi-Miki, Shinobu; Kagitani-Suyama, Akemi; Fujiwara, Tamio.
Afiliación
  • Akiyama T; Shionogi Pharmaceutical Research Center, Shionogi & Co., Ltd., 3-1-1 Futaba-cho, Toyonaka-shi, Osaka 561-0825, Japan. Electronic address: toshiyuki.akiyama@shionogi.co.jp.
  • Johns BA; GlaxoSmithKline Research & Development, Infectious Diseases Therapeutic Area Unit, Five Moore Drive, Research Triangle Park, NC 27709, United States.
  • Taoda Y; Shionogi Pharmaceutical Research Center, Shionogi & Co., Ltd., 3-1-1 Futaba-cho, Toyonaka-shi, Osaka 561-0825, Japan.
  • Yoshida H; Shionogi Pharmaceutical Research Center, Shionogi & Co., Ltd., 3-1-1 Futaba-cho, Toyonaka-shi, Osaka 561-0825, Japan.
  • Taishi T; Shionogi Pharmaceutical Research Center, Shionogi & Co., Ltd., 3-1-1 Futaba-cho, Toyonaka-shi, Osaka 561-0825, Japan.
  • Kawasuji T; Shionogi Pharmaceutical Research Center, Shionogi & Co., Ltd., 3-1-1 Futaba-cho, Toyonaka-shi, Osaka 561-0825, Japan.
  • Murai H; Shionogi Pharmaceutical Research Center, Shionogi & Co., Ltd., 3-1-1 Futaba-cho, Toyonaka-shi, Osaka 561-0825, Japan.
  • Yoshinaga T; Shionogi Pharmaceutical Research Center, Shionogi & Co., Ltd., 3-1-1 Futaba-cho, Toyonaka-shi, Osaka 561-0825, Japan.
  • Sato A; Shionogi Pharmaceutical Research Center, Shionogi & Co., Ltd., 3-1-1 Futaba-cho, Toyonaka-shi, Osaka 561-0825, Japan.
  • Seki T; Shionogi Pharmaceutical Research Center, Shionogi & Co., Ltd., 3-1-1 Futaba-cho, Toyonaka-shi, Osaka 561-0825, Japan.
  • Koyama M; Shionogi Pharmaceutical Research Center, Shionogi & Co., Ltd., 3-1-1 Futaba-cho, Toyonaka-shi, Osaka 561-0825, Japan.
  • Miki S; Shionogi Pharmaceutical Research Center, Shionogi & Co., Ltd., 3-1-1 Futaba-cho, Toyonaka-shi, Osaka 561-0825, Japan.
  • Kawauchi-Miki S; Shionogi Pharmaceutical Research Center, Shionogi & Co., Ltd., 3-1-1 Futaba-cho, Toyonaka-shi, Osaka 561-0825, Japan.
  • Kagitani-Suyama A; Shionogi Pharmaceutical Research Center, Shionogi & Co., Ltd., 3-1-1 Futaba-cho, Toyonaka-shi, Osaka 561-0825, Japan.
  • Fujiwara T; Shionogi Pharmaceutical Research Center, Shionogi & Co., Ltd., 3-1-1 Futaba-cho, Toyonaka-shi, Osaka 561-0825, Japan.
Bioorg Med Chem Lett ; 111: 129902, 2024 Oct 01.
Article en En | MEDLINE | ID: mdl-39059564
ABSTRACT
Integrase strand transfer inhibitors (INSTIs) are the most prescribed anchor drug in antiretroviral therapy. Today, there is an increasing need for long-acting treatment of HIV-1 infection. Improving drug pharmacokinetics and anti-HIV-1 activity are key to developing more robust inhibitors suitable for long-acting formulations, but 2nd-generation INSTIs have chiral centers, making it difficult to conduct further exploration. In this study, we designed aza-tricyclic and aza-bicyclic carbamoyl pyridone scaffolds which are devoid of the problematic hemiaminal stereocenter present in dolutegravir (DTG). This scaffold hopping made it easy to introduce several substituents, and evolving structure-activity studies using these scaffolds resulted in several leads with promising properties.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Piridonas / Diseño de Fármacos / VIH-1 / Inhibidores de Integrasa VIH / Integrasa de VIH Límite: Humans Idioma: En Revista: Bioorg Med Chem Lett Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2024 Tipo del documento: Article Pais de publicación: Reino Unido

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Piridonas / Diseño de Fármacos / VIH-1 / Inhibidores de Integrasa VIH / Integrasa de VIH Límite: Humans Idioma: En Revista: Bioorg Med Chem Lett Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2024 Tipo del documento: Article Pais de publicación: Reino Unido