- Photodissociation of B-N Lewis adducts: A partially fused trinaphthylborane with dual fluorescence
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The synthesis of a planarized trinaphthylborane with partially fused structure is presented. This compound shows not only high chemical and thermal stability but also sufficient Lewis acidity to form Lewis adducts with pyridine derivatives in solution. The B-N Lewis adducts exhibit unprecedented photodissociation behavior in the excited state, reminiscent of the photogeneration of carbenium ions from triarylmethane leuco dyes. Consequently, these B-N Lewis adducts exhibit dual fluorescence emission arising from the initial tetracoordinate B-N adducts and the photodissociated tricoordinate boranes.
- Matsuo, Kyohei,Saito, Shohei,Yamaguchi, Shigehiro
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- KRAS G12C INHIBITORS
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The present invention relates to compounds that, inhibit KRas G12C, In particular, the present invention relates to compounds that irreversibly inhibit the activity of KRas G12C, pharmaceutical compositions comprising the compounds and methods of use therefor.
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Paragraph 0433-0434
(2020/03/23)
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- Divergent intramolecular reactions between phosphines and alkynes
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A divergent intramolecular reaction of phosphine tethered alkyne in protic solvent was developed. This provided a novel and simple access to a large variety of (Z)-alkenylphosphine oxides and phospholane oxides. Our preliminary studies suggested that these divergent reactions are closely related to the reaction condition and molecular structure. A possible mechanism of C-P bond cleavage of a pentacoordinated hydroxyphosphorane intermediate was proposed.
- Song, Yanying,Wang, Lili,Duan, Zheng,Mathey, Fran?ois
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supporting information
p. 329 - 332
(2019/06/18)
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- Identification of the Clinical Development Candidate MRTX849, a Covalent KRASG12CInhibitor for the Treatment of Cancer
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Capping off an era marred by drug development failures and punctuated by waning interest and presumed intractability toward direct targeting of KRAS, new technologies and strategies are aiding in the target's resurgence. As previously reported, the tetrahydropyridopyrimidines were identified as irreversible covalent inhibitors of KRASG12C that bind in the switch-II pocket of KRAS and make a covalent bond to cysteine 12. Using structure-based drug design in conjunction with a focused in vitro absorption, distribution, metabolism and excretion screening approach, analogues were synthesized to increase the potency and reduce metabolic liabilities of this series. The discovery of the clinical development candidate MRTX849 as a potent, selective covalent inhibitor of KRASG12C is described.
- Fell, Jay B.,Fischer, John P.,Baer, Brian R.,Blake, James F.,Bouhana, Karyn,Briere, David M.,Brown, Karin D.,Burgess, Laurence E.,Burns, Aaron C.,Burkard, Michael R.,Chiang, Harrah,Chicarelli, Mark J.,Cook, Adam W.,Gaudino, John J.,Hallin, Jill,Hanson, Lauren,Hartley, Dylan P.,Hicken, Erik J.,Hingorani, Gary P.,Hinklin, Ronald J.,Mejia, Macedonio J.,Olson, Peter,Otten, Jennifer N.,Rhodes, Susan P.,Rodriguez, Martha E.,Savechenkov, Pavel,Smith, Darin J.,Sudhakar, Niranjan,Sullivan, Francis X.,Tang, Tony P.,Vigers, Guy P.,Wollenberg, Lance,Christensen, James G.,Marx, Matthew A.
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supporting information
p. 6679 - 6693
(2020/04/20)
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- Paving the Way to Novel Phosphorus-Based Architectures: A Noncatalyzed Protocol to Access Six-Membered Heterocycles
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Phosphorus-based heterocycles provide access to materials with properties that are inaccessible from all-carbon architectures. The unique hybridization of phosphorus gives rise to electron-accepting capacities, a large variety of coordination reactions, a
- Romero-Nieto, Carlos,Lpez-Andarias, Alicia,Egler-Lucas, Carolina,Gebert, Florian,Neus, Jens-Peter,Pilgram, Oliver
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supporting information
p. 15872 - 15875
(2016/01/28)
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- The metalation of 1- and 2-(trifluoromethyl)naphthalenes: Noteworthy site selectivities
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This article provides insight into the various factors by which electronegative substituents affect the kinetic acidity of arenes and, more specifically, naphthalenes. Both 1- and 2-(trifluoromethyl)naphthalenes were consecutively treated with an organometallic or lithium dialkylamide-type base and carbon dioxide. Due to single electron-transfer triggered side reactions, the yields of (trifluoromethyl)naphthoic acids were moderate to poor. 1-(Trifluoromethyl)naphthalene was exclusively attacked at the 2-position as expected. The 2-isomer reacted with tert-butyllithium in the presence of potassium tert-butoxide solely at the 1-position, but with sec-butyllithium in the presence of N,N,N′,N′-tetramethylethylene-diamine concomitantly at the 3- and 4-positions. Authentic samples of the key acids 1, 4, 5 and 6 were prepared based on independent, unambiguous methods.
- Cottet, Fabrice,Castagnetti, Eva,Schlosser, Manfred
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p. 798 - 803
(2007/10/03)
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