1485-22-9Relevant articles and documents
Human serum albumin binding assay based on displacement of a non selective fluorescent inhibitor
Thorarensen, Atli,Sarver, Ronald W.,Tian, Fang,Ho, Andrea,Romero, Donna L.,Marotti, Keith R.
, p. 4646 - 4649 (2007)
In this paper, we describe a fluorescent antibacterial analog, 6, with utility as a competition probe to determine affinities of other antibacterial analogs for human serum albumin (HSA). Analog 6 bound to HSA with an affinity of 400 ± 100 nM and the fluorescence was environmentally sensitive. With 370 nm excitation, environmental sensitivity was indicated by a quenching of the 530 nm emission when the probe bound to HSA. Displacement of dansylsarcosine from HSA by 6 indicated it competed with compounds that bound at site II (ibuprofen binding site) on HSA. Analog 6 also shifted the NMR peaks of an HSA bound oleic acid molecule that itself was affected by compounds that bound at site II. In addition to binding at site II, 6 interacted at site I (warfarin binding site) as indicated by displacement of dansylamide and the shifting of NMR peaks of an HSA bound oleic acid molecule affected by warfarin site binding. Additional evidence for multiple site interaction was discovered when a percentage of 6 could be displaced by either ibuprofen or phenylbutazone. A competition assay was established using 6 to determine relative affinities of other antibacterial inhibitors for HSA.
Palladium-catalyzed acylation of a 1,2-disubstituted 3-indolylzine chloride
Faul, Margaret M.,Winneroski, Leonard L.
, p. 4749 - 4752 (1997)
3-Acylindoles were prepared by palladium catalyzed coupling of an acid sensitive 1,2-disubstituted 3-indolylzinc chloride with a number of acid chlorides to give the corresponding ketones in 33-74% yields.
Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides
Ong, Derek Yiren,Yen, Zhihao,Yoshii, Asami,Revillo Imbernon, Julia,Takita, Ryo,Chiba, Shunsuke
supporting information, p. 4992 - 4997 (2019/03/13)
New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX2). Use of a different halide on ZnX2 dictates the selectivity, wherein the NaH-ZnI2 system delivers alcohols and NaH-ZnCl2 gives amines. Extensive mechanistic studies by experimental and theoretical approaches imply that polymeric zinc hydride (ZnH2)∞ is responsible for alcohol formation, whereas dimeric zinc chloride hydride (H?Zn?Cl)2 is the key species for the production of amines.
Cycloaddition of in Situ Formed Azaoxyallyl Cations with 2-Alkenylindoles: An Approach to Tetrahydro-β-carbolinones
Zhang, Kaifan,Xu, Xiaoying,Zheng, Jiuan,Yao, Hequan,Huang, Yue,Lin, Aijun
supporting information, p. 2596 - 2599 (2017/05/24)
A novel [3 + 3] cycloaddition between in situ formed azaoxyallyl cations and 2-alkenylindoles has been developed. This concise method allows the efficient construction of a series of tetrahydro-β-carbolinones in good yields under mild conditions. Gram-sca
Zinc-Catalyzed Alkyne Oxidation/C-H Functionalization: Highly Site-Selective Synthesis of Versatile Isoquinolones and β-Carbolines
Li, Long,Zhou, Bo,Wang, Yong-Heng,Shu, Chao,Pan, Yi-Fei,Lu, Xin,Ye, Long-Wu
supporting information, p. 8245 - 8249 (2015/07/07)
An efficient zinc(II)-catalyzed alkyne oxidation/C￡H functionalization sequence was developed, thus leading to highly site-selective synthesis of a variety of isoquinolones and β-carbolines. Importantly, in contrast to the well-established gold-catalyzed intermolecular alkyne oxidation, over-oxidation can be completely suppressed in this system and the reaction most likely proceeds by a Friedel-Crafts-type pathway. Mechanistic studies and theoretical calculations are described.
