107033-46-5Relevant academic research and scientific papers
Concise synthesis of acetal-protected syn 1,3-diols by a tandem hemiacetal formation/Tsuji-Trost reaction
Wang, Liang,Menche, Dirk
, p. 9425 - 9427 (2012)
Designed, developed, and applied: A novel domino sequence was used for the rapid assembly of acetal-protected syn 1,3-diols. The convergent synthesis of a polyol fragment of the macrolide antibiotic RK-397 demonstrates that this method is suitable for the rapid and stereoselective preparation of polyketide-type diol motifs.
Computationally guided discovery of a reactive, hydrophilic: Trans -5-oxocene dienophile for bioorthogonal labeling
Lambert, William D.,Scinto, Samuel L.,Dmitrenko, Olga,Boyd, Samantha J.,Magboo, Ronald,Mehl, Ryan A.,Chin, Jason W.,Fox, Joseph M.,Wallace, Stephen
, p. 6640 - 6644 (2017)
The use of organic chemistry principles and prediction techniques has enabled the development of new bioorthogonal reactions. As this "toolbox" expands to include new reaction manifolds and orthogonal reaction pairings, the continued development of existing reactions remains an important objective. This is particularly important in cellular imaging, where non-specific background fluorescence has been linked to the hydrophobicity of the bioorthogonal moiety. Here we report that trans-5-oxocene (oxoTCO) displays enhanced reactivity and hydrophilicity compared to trans-cyclooctene (TCO) in the tetrazine ligation reaction. Aided by ab initio calculations we show that the insertion of a single oxygen atom into the trans-cyclooctene (TCO) ring system is sufficient to impart aqueous solubility and also results in significant rate acceleration by increasing angle strain. We demonstrate the rapid and quantitative cycloaddition of oxoTCO using a water-soluble tetrazine derivative and a protein substrate containing a site-specific genetically encoded tetrazine moiety both in vitro and in vivo. We anticipate that oxoTCO will find use in studies where hydrophilicity and fast bioconjugation kinetics are paramount.
Synthesis of (R)-(-)-argentilactone
Hansen, Trond Vidar
, p. 547 - 550 (2002)
A synthesis of (R)-(-)-argentilactone is reported starting from the (S)-enantiomer of glycidol. The synthesis is based on ring closing metathesis of the acrylic ester of (R)-1-O-(tert-butyldiphenylsilyl)-4-penten-1,2-diol 4.
Total Synthesis of (R)-Argentilactone and (R)-Goniothalamin Using a Free-Radical Photoredox Approach to α,β-Unsaturated δ-Lactones
Fuentes-Pantoja, Francisco J.,Cordero-Vargas, Alejandro
supporting information, p. 4433 - 4439 (2021/08/20)
α,β-Unsaturated δ-lactones are structural motifs found in diverse pharmacologically active natural products. In fact, the unsaturated lactone is often responsible for the biological activity. Herein, we report a new approach for the syntheses of (R)-argentilactone and (R)- goniothalamin based on a photoredox intermolecular iodolactonization mediated by a photoredox process. This new approach, already employed in our research group, stands as a new methodology to achieve several natural products containing α,β-Unsaturated δ-lactones.
CD73 INHIBITORS
-
Page/Page column 42, (2019/09/18)
The present invention provides 5-[5]-[2-cycloa Ikyl ]-6-pyridazin-3-yl ]- IH-pyrimidine-2,4-dione compounds, or pharmaceutically acceptable salts thereof, that inhibit the activity of CD73 and are useful in treating cancer. (Formula (I))
COMPOUNDS AND METHODS FOR THE TREATMENT OF PARASITIC DISEASES
-
Page/Page column 81; 82, (2018/10/19)
Provided herein are compounds useful for the treatment of various parasitic diseases. These compounds, as well as pharmaceutically acceptable salts thereof may be formulated in pharmaceutical compostions, veterinary compositions and may be used in methods
Synthesis of Vicinal Dichlorides via Activation of Aliphatic Terminal Epoxides with Triphosgene and Pyridine
Cleveland, Alexander H.,Fronczek, Frank R.,Kartika, Rendy
, p. 3367 - 3377 (2018/03/26)
Herein we report a novel synthetic reaction to convert unactivated terminal aliphatic epoxide to alkyl vicinal dichloride based on triphosgene-pyridine activation. Our methodology is operationally simple and readily tolerated by a broad of scope of substrates as well as protecting groups. Furthermore, these mild conditions generally yield clean reaction mixtures that are free of byproducts upon aqueous workup.
Development of Hybrid Phospholipid Mimics as Effective Agonists for Liver Receptor Homologue-1
Flynn, Autumn R.,Mays, Suzanne G.,Ortlund, Eric A.,Jui, Nathan T.
supporting information, p. 1051 - 1056 (2018/09/21)
The orphan nuclear receptor Liver Receptor Homologue-1 (LRH-1) is an emerging drug target for metabolic disorders. The most effective known LRH-1 modulators are phospholipids or synthetic hexahydropentalene compounds. While both classes have micromolar ef
Design, synthesis, and cytotoxicity of stabilized mycolactone analogs
Babu, Vaddela Sudheer,Zhou, Ya,Kishi, Yoshito
supporting information, p. 1274 - 1277 (2017/06/21)
On exposure to visible light, mycolactone A/B, the causative toxin of Buruli ulcer, rearranges to a mixture of four photo-mycolactones apparently via a rare photochemically-induced [4πs?+?2πa] cycloaddition. In
Antimalarial diterpenoid dimers of a new carbon skeleton from Aphanamixis grandifolia
Zhang, Hua,Liu, Jia,Gan, Li-She,Dalal, Seema,Cassera, Maria B.,Yue, Jian-Min
supporting information, p. 957 - 962 (2016/01/15)
Chemical investigation into the minor constituents of Aphanamixis grandifolia yielded three new diterpenoid dimers, aphadilactones E-G (1-3) featuring a new carbon skeleton. Their structures and absolute configurations were fully established by comprehensive spectroscopic data analysis and ECD calculation. Discovery of another two new dimers (4 and 5) suggested the structure of recently reported aphanamene A to be re-investigated. Compounds 1-5 showed moderate antimalarial activities with low micromolar IC50 values.
