439919-46-7Relevant articles and documents
Synthesis of sesquiterpene antitumor lactones. Studies directed toward the total synthesis of pentalenolactone. Intramolecular ene reaction
Plavac,Heathcock
, p. 2115 - 2118 (1979)
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Thromboxane receptor active analogues based on the 6-oxabicyclo[3.2.1]octane ring system
Muir,Jones,Will,Winwick,Peesapati,Wilson,Griffiths,Nicholson,Taylor,Sawyer,Blake
, p. 609 - 624 (1993)
Prostanoid analogues with a 6-oxabicyclo[3.2.1]octane ring and 3 different types of ω-chain have been synthesized and evaluated for biological activity on thromboxane A2 (TXA2) receptors and prostaglandin I2 (PGI2) receptors. The standard ω-chain analogue 34b is a TXA2 receptor agonist approximately 10-fold less potent than U46619 3, the standard agonist. The O-diphenylmethyloximino-ω'-chain analogue 32 gives a PGI2-like agonist ~5-fold less active than EP 157, the most active molecule in this class. Conversely, 4-arylsemicarbazone ω-chain analogues 35a and 35b show TXA2 antagonism comparable to that obtained with bicyclo[2.2.2]octane and bicyclo[2.2.1]heptane systems containing this type of ω-chain (eg EP 092).
Trisequential photooxygenation reaction: Application to the synthesis of carbasugars
Baran, Arif,Aydin, Gokay,Savran, Tahir,Sahin, Ertan,Balci, Metin
, p. 4350 - 4353 (2013)
4,5-Dimethylenecyclohex-1-ene was subjected to a photooxygenation reaction to introduce oxygen functionalities. The endoperoxide obtained underwent an ene-reaction to form hydroperoxides with 1,3-diene structures. Further addition of singlet oxygen to the
Structure-Based Design of Highly Potent HIV-1 Protease Inhibitors Containing New Tricyclic Ring P2-Ligands: Design, Synthesis, Biological, and X-ray Structural Studies
Ghosh, Arun K.,Kovela, Satish,Osswald, Heather L.,Amano, Masayuki,Aoki, Manabu,Agniswamy, Johnson,Wang, Yuan-Fang,Weber, Irene T.,Mitsuya, Hiroaki
, p. 4867 - 4879 (2020/05/13)
We describe here design, synthesis, and biological evaluation of a series of highly potent HIV-1 protease inhibitors containing stereochemically defined and unprecedented tricyclic furanofuran derivatives as P2 ligands in combination with a variety of sulfonamide derivatives as P2′ ligands. These inhibitors were designed to enhance the ligand-backbone binding and van der Waals interactions in the protease active site. A number of inhibitors containing the new P2 ligand, an aminobenzothiazole as the P2′ ligand and a difluorophenylmethyl as the P1 ligand, displayed very potent enzyme inhibitory potency and also showed excellent antiviral activity against a panel of highly multidrug-resistant HIV-1 variants. The tricyclic P2 ligand has been synthesized efficiently in an optically active form using enzymatic desymmetrization of meso-1,2-(dihydroxymethyl)cyclohex-4-ene as the key step. We determined high-resolution X-ray structures of inhibitor-bound HIV-1 protease. These structures revealed extensive interactions with the backbone atoms of HIV-1 protease and provided molecular insights into the binding properties of these new inhibitors.
Iron-Catalyzed Ring-Closing C?O/C?O Metathesis of Aliphatic Ethers
Biberger, Tobias,Makai, Szabolcs,Lian, Zhong,Morandi, Bill
supporting information, p. 6940 - 6944 (2018/05/14)
Among all metathesis reactions known to date in organic chemistry, the metathesis of multiple bonds such as alkenes and alkynes has evolved into one of the most powerful methods to construct molecular complexity. In contrast, metathesis reactions involving single bonds are scarce and far less developed, particularly in the context of synthetically valuable ring-closing reactions. Herein, we report an iron-catalyzed ring-closing metathesis of aliphatic ethers for the synthesis of substituted tetrahydropyrans and tetrahydrofurans, as well as morpholines and polycyclic ethers. This transformation is enabled by a simple iron catalyst and likely proceeds via cyclic oxonium intermediates.
