36054-00-9Relevant academic research and scientific papers
Peptidomimetics and Methods of Using the Same
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, (2018/03/25)
Disclosed herein are compounds useful for modulating the mu-opioid receptor (“MOR”) and/or delta-opioid receptor (“DOR”), and methods of using these compounds to treat diseases and conditions, such as pain. In particular, disclosed herein are compounds of
Asymmetric Synthesis of Cyclopentene-Fused Tetrahydroquinolines via N-Heterocyclic Carbene Catalyzed Domino Reactions
Zhao, Long,Li, Sun,Wang, Lei,Yu, Shun,Raabe, Gerhard,Enders, Dieter
, p. 2523 - 2532 (2018/05/28)
A new strategy for the N-heterocyclic carbene catalyzed asymmetric synthesis of cyclopentene-fused tetrahydroquinoline derivatives has been developed. The one-pot organocatalytic domino protocol allows a direct entry to the characteristic cyclopenta[ c ]tetrahydroquinoline core of many alkaloids and some potential drugs employing readily available quinolinone and enal substrates in good domino yields and stereoselectivities.
Synthesis of new tricyclic 5,6-dihydro-4H-benzo[b][1,2,4]tri-azolo[1,5-d][1,4]diazepine derivatives by [3+ + 2]-cyclo-addition/rearrangement reactions
Luan, Lin-bo,Song, Zi-jie,Li, Zhi-ming,Wang, Quan-rui
, p. 1826 - 1833 (2018/08/21)
Two new series of tricyclic heterocycles, namely 5,6-dihydro-4H-benzo[b][1,2,4]triazolo[1,5-d][1,4]diazepinium salts 10 and the related neutral, free bases 13 were synthesized from 4-acetoxy-1-acetyl-4-phenylazo-1,2,3,4-tetrahydroquinolines 8 and nitriles 9 in the presence of aluminium chloride by the [3+ + 2]-cycloaddition reaction of the in situ generated azocarbenium intermediates 14 followed by a ring-expansion rearrangement. In the rearrangement reaction, the phenyl substituent in the initially formed spiro-triazolium adducts 16 underwent a [1,2]-migration from C(3) to the electron-deficient N(2). This led to the ring expansion from 6-membered piperidine to 7-membered diazepine furnishing the tricyclic 1,2,4-triazole-fused 1,4-benzodiazepines.
Superacid-catalyzed tandem Meyer–Schuster rearrangement/intramolecular hydroamination of o-anilinopropargyl alcohols for the synthesis of 2,3-dihydro-4(1H)-quinolones
Sun, Guofeng,Cheng, Fengkai,Tao, Ruiheng,Sun, Yuxing,Pan, Jinpeng,Zhu, Yaohua,Wang, Zhonghua,Wu, Fanhong,Yin, Yan
, p. 1249 - 1256 (2016/08/16)
A TfOH-catalyzed synthesis of 2,3-dihydro-4(1H)-quinolones from o-anilinopropargyl alcohols was developed. Studies of N-protecting groups and substituents in phenyl rings showed that diverse groups could be applied. By controlling the catalyst loading, o-anilinopropargyl alcohols underwent the expected transformation smoothly to produce N-protected or N-deprotected 2,3-dihydro-4 (1H)-quinolones in good yields. This transformation probably involved a tandem Meyer–Schuster rearrangement/intramolecular hydroamination reaction process.
Asymmetric Synthesis and in Vitro and in Vivo Activity of Tetrahydroquinolines Featuring a Diverse Set of Polar Substitutions at the 6 Position as Mixed-Efficacy μ Opioid Receptor/δ Opioid Receptor Ligands
Bender, Aaron M.,Griggs, Nicholas W.,Anand, Jessica P.,Traynor, John R.,Jutkiewicz, Emily M.,Mosberg, Henry I.
, p. 1428 - 1435 (2015/09/01)
We previously reported a small series of mixed-efficacy μ opioid receptor (MOR) agonist/δ opioid receptor (DOR) antagonist peptidomimetics featuring a tetrahydroquinoline scaffold and showed the promise of this series as effective analgesics after intrape
Quinolinoneacetic acid derivatives as novel glutathione S-transferase P1-1 inhibitors: Insights into the interaction modes by molecular modeling
Wang, Jian,Wang, Shao-Jie,Song, Dan-Dan,Jing, Yong-Kui,Cheng, Mao-Sheng
, p. 2823 - 2826 (2012/10/30)
Glutathione S-transferase P1-1 (GSTP1-1, EC 2.5.1.18) is generally conceived to be an important player in the acquired resistance of tumor to anticancer agents, thus a series of quinolinoneacetic acid derivatives were synthesized and their inhibitory effe
Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones
Fang, Yuesi,Rogness, Donald C.,Larock, Richard C.,Shi, Feng
, p. 6262 - 6270 (2012/09/22)
N-Unsubstituted β-lactams react with a molecule of aryne by insertion into the amide bond to form a 2,3-dihydroquinolin-4-one, which subsequently reacts with another molecule of aryne to form an acridone by extrusion of a molecule of ethylene. 2,3-Dihydroquinolin-4-ones react under the same reaction conditions to afford identical results. This is the first example of ethylene extrusion in aryne chemistry.
Synthesis of 2,3-dihydro-4(1H)-quinolones and the corresponding 4(1H)-quinolones via low-temperature fries rearrangement of N-arylazetidin-2- ones
Lange, Jens,Bissember, Alex C.,Banwell, Martin G.,Cade, Ian A.
, p. 454 - 470 (2011/10/09)
N-Arylazetidin-2-ones of the general form 1, which are readily prepared by GoldbergBuchwald-type copper-catalyzed coupling of N-unsubstituted azetidin-2-ones with the relevant aryl halide or using Mitsunobu cyclization processes, undergo smooth Fries-rearrangement in triflic acid at 018°C to give the isomeric 2,3-dihydro-4(1H)-quinolones (2). Dehydrogenation of the latter compounds using 10% Pd on C in 1.0M aqueous sodium hydroxide/propan-2-ol mixtures at ca. 82°C provides the corresponding 4(1H)-quinolones (3).
Transition metal mediated construction of pyrrole ring on 2,3-dihydroquinolin-4(1H)-one: Synthesis and pharmacological evaluation of novel tricyclic heteroarenes
Layek, Mohosin,Reddy M., Appi,Dhanunjaya Rao,Alvala, Mallika,Arunasree,Islam, Aminul,Mukkanti,Iqbal, Javed,Pal, Manojit
supporting information; experimental part, p. 1004 - 1007 (2011/03/23)
A facile two-step method for the construction of fused pyrrole ring leading to 5-substituted 2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinolin-1-ones via C-C followed by intramolecular C-N bond forming reaction is described. In vitro pharmacological evaluation and
