622863-63-2Relevant academic research and scientific papers
Non-Bonding Electron Pair versus π-Electrons in Solution Phase Halogen Bond Catalysis: Povarov Reaction of 2-Vinylindoles and Imines
Suzuki, Takumi,Kuwano, Satoru,Arai, Takayoshi
supporting information, p. 3208 - 3212 (2020/07/04)
The non-bonding electron pair (n-pair) of heteroatoms and π-electrons are both efficient halogen bond (XB) acceptors. In solid and gas phase studies, n-pairs generally prevail over π-bonding orbitals as XB acceptors, whereas few studies have been conducte
Catalysis Based on C?I???π Halogen Bonds: Electrophilic Activation of 2-Alkenylindoles by Cationic Halogen-Bond Donors for [4+2] Cycloadditions
Kuwano, Satoru,Suzuki, Takumi,Yamanaka, Masahiro,Tsutsumi, Ryosuke,Arai, Takayoshi
supporting information, p. 10220 - 10224 (2019/07/04)
Homo- and cross-[4+2] cycloadditions of 2-alkenylindoles, catalyzed by cationic halogen-bond donors, were developed. Under mild reaction conditions, 3-indolyl-substituted tetrahydrocarbazole derivatives were obtained in good to excellent yields. Experimental and quantum calculation studies revealed that the electrophilic activation of 2-alkenylindoles was achieved by C?I???π halogen bonds.
Synthesis of 2-Substituted Indoles through Visible Light-Induced Photocatalytic Cyclizations of Styryl Azides
Xia, Xu-Dong,Xuan, Jun,Wang, Qiang,Lu, Liang-Qiu,Chen, Jia-Rong,Xiao, Wen-Jing
, p. 2807 - 2812 (2016/02/18)
A visible light-induced photocatalytic intramolecular cyclization of styryl azides has been developed in the presence of the ruthenium complex Ru(bpy)3Cl2 (0.5 mol%) as photocatalyst at room temperature. The present photocatalytic strategy features operational simplicity as well as high functional group tolerance, and provides a facile access to various 2-substituted N-free indoles in good to excellent yields. Importantly, the present process can employ sunlight as the light source to afford the corresponding products without loss of reaction efficiency.
Convenient synthesis of tetrahydro-γ-carbolines and tetrahydroquinolines through a chemo- and regioselectivity switch by a broonsted acid catalyzed, one-pot, multicomponent reaction
Cheng, Hong-Gang,Chen, Cai-Bao,Tan, Fen,Chang, Ning-Jie,Chen, Jia-Rong,Xiao, Wen-Jing
supporting information; experimental part, p. 4976 - 4980 (2010/11/03)
An efficient, one-pot, multicomponent reaction of aldehydes 1, p-methoxyaniline (2a), and 2-vinylindoles 3 was developed. This approach provides a practical approach to synthetically and biologically significant tetrahydro-γ-carboline and tetrahydroquinol
Synthesis, NMR conformational analysis and pharmacological evaluation of 7,7a,13,14-tetrahydro-6H-cyclobuta[b]pyrimido[1,2-a:3,4-a′]diindole analogues as melatonin receptor ligands
Attia, Mohamed I.,Gueclue, Deniz,Hertlein, Barbara,Julius, Justin,Witt-Enderby, Paula A.,Zlotos, Darius P.
, p. 2129 - 2137 (2008/03/14)
A structure for the self-condensation product of 2-(1H-indol-2-yl)ethyl tosylate 2a, previously proposed as 6,7,14,15-tetrahydro-15aH-azocino[1,2-a:6,5- b]diindole 3a, was revised based on the 13C-2D-INADEQUATE experiment, and proved to be 7,7a,13,14-tetrahydro-6H-cyclobuta[b]pyrimido[1,2-a:3,4- a′]diindole 4a. A mechanism for the unexpected formation of this novel hexacyclic heterocycle was proposed and its NMR solution structure was elucidated. Five derivatives of the title ring skeleton 12-16 designed as melatonin receptor ligands were synthesized and their affinities for the human MT1 and MT2 receptors were determined. Both butyramides 13 and 15, as well as the non-methoxy acetamide 12 exhibited micromolar binding affinities for both receptors being slightly MT2 selective. The methoxy acetamide 14 showed the best pharmacological profile exhibiting a five times higher affinity for MT1 (Ki = 49 nM) than for MT2 (Ki = 246 nM) receptor. This journal is The Royal Society of Chemistry.
4-Phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione inhibitors of the checkpoint kinase Wee1. structure-activity relationships for chromophore modification and phenyl ring substitution
Palmer, Brian D.,Thompson, Andrew M.,Booth, R. John,Dobrusin, Ellen M.,Kraker, Alan J.,Lee, Ho H.,Lunney, Elizabeth A.,Mitchell, Lorna H.,Ortwine, Daniel F.,Smaill, Jeff B.,Swan, Leesa M.,Denny, William A.
, p. 4896 - 4911 (2007/10/03)
High-throughput screening has identified a novel class of inhibitors of the checkpoint kinase Wee1, which have potential for use in cancer chemotherapy. These inhibitors are based on a 4-phenylpyrrolo[3,4-c]-carbazole-1,3(2H,6H)- dione template and have been shown by X-ray crystallography to bind at the ATP site of the enzyme. An extensive study of the effects of substitution around this template has been carried out, which has identified substituents which lead to improvements in potency and selectivity for Wee1. While retention of the maleimide ring and pendant 4-phenyl group is necessary for potency, replacement of the carbazole nitrogen by oxygen is well tolerated and results in improved Wee1 selectivity against the related checkpoint kinase Chk1. Wee1 potency and selectivity are also enhanced by the incorporation of lipophilic functionality at the 2′-position of the 4-phenyl ring, and Wee1 selectivity against Chk1 is favored by C3-C5 alkyl substitution of the carbazole nitrogen. These studies provide a basis for the design of active analogues of the pyrrolocarbazole lead with improved physical properties.
