31180-83-3Relevant academic research and scientific papers
Conformational-Analysis-Guided Discovery of 2,3-Disubstituted Pyridine IDO1 Inhibitors
Anandam, Aravind,Balog, Aaron,Borzilleri, Robert,Cherney, Emily C.,D'arienzo, Celia J.,Delpy, Diane,Dhar, Gopal,Discenza, Lorell N.,Fereshteh, Mark,Foster, Kimberly A.,Grubb, Mary F.,Gullo-Brown, Johnni,Guo, Weiwei,Gupta, Anuradha,Hong, Zhenqiu,Huang, Audris,Huang, Christine,Hunt, John T.,Johnston, Kathy A.,Kempson, James,Kopcho, Lisa,Li, Xin,Lin, Tai-An,Mahankali, Sandeep,Maley, Derrick,Mariappan, T. Thanga,Mathur, Arvind,Murali, Venkata,Nimje, Roshan Y.,Padmanabhan, Shweta,Pattasseri, Shabeerali,Rajanna, Prabhakar,Rampulla, Richard,Ranasinghe, Asoka,Seitz, Steven,Shan, Weifang,Stefanski, Kevin,Traeger, Sarah C.,Vite, Gregory,Williams, David,Yang, Zheng,Zhang, Liping,Zhu, Xiao
, p. 1143 - 1150 (2021/07/19)
IDO1 inhibitors have shown promise as immunotherapies for the treatment of a variety of cancers, including metastatic melanoma and renal cell carcinoma. We recently reported the identification of several novel heme-displacing IDO1 inhibitors, including the clinical molecules linrodostat (BMS-986205) and BMS-986242. Both molecules contain quinolines that, while being present in successful medicines, are known to be potentially susceptible to oxidative metabolism. Efforts to swap this quinoline with an alternative aromatic system led to the discovery of 2,3-disubstituted pyridines as suitable replacements. Further optimization, which included lowering ClogP in combination with strategic fluorine incorporation, led to the discovery of compound 29, a potent, selective IDO1 inhibitor with robust pharmacodynamic activity in a mouse xenograft model.
Total synthesis of (±)-β-chamigrene and (±)-laurencenone C via Ireland ester Claisen rearrangement and an intramolecular type II carbonyl ene reaction sequence
Srikrishna,Babu, R. Ramesh
, p. 10501 - 10506 (2008/12/23)
A combination of Ireland ester Claisen rearrangement and intramolecular type II carbonyl ene reactions were exploited for the total synthesis of chamigrenes containing a quaternary carbon atom next to the spirocentre in spiro[5.5]undecane.
Total syntheses of (±)-α-acorenol, β-acorenol, α-epi-acorenol and β-epi-acorenol via an Ireland ester Claisen rearrangement and RCM reaction sequence
Srikrishna,Babu, R. Ramesh
, p. 6916 - 6919 (2008/02/13)
Total syntheses of (±)-α- and β-acorenols and (±)-α- and β-epi-acorenols, spiro[4.5]decane sesquiterpenes, isolated from the western Australian sandalwood oil, have been accomplished employing a combination of Ireland ester Claisen rearrangement and RCM r
Protection of the carbonyl group as 1,2,4-trioxane and its regeneration under basic conditions
Singh, Chandan,Malik, Heetika
, p. 5673 - 5676 (2007/10/03)
(Chemical Equation Presented) An experimental protocol demonstrating the protection of the carbonyl group as 1,2,4-trioxane, the stability of the protecting group under a variety of reaction conditions, and the regeneration of the carbonyl group with Triton B in THF at room temperature is presented. The method provides a useful alternative for the protection of carbonyl compounds having acid-sensitive moieties.
