67278-27-7Relevant articles and documents
Hypervalent iodine(III) induced intramolecular cyclization of substituted phenol ethers bearing an alkyl azido sidechain-a novel synthesis of quinone imine ketals
Kita, Yasuyuki,Egi, Masahiro,Okajima, Akiko,Ohtsubo, Makoto,Takada, Takeshi,Tohma, Hirofumi
, p. 1491 - 1492 (1996)
A novel and efficient synthesis of quinone imine ketals from substituted phenol ethers bearing an alkyl azido sidechain using a hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA), is described.
Synthesis and biological evaluation of C-ring truncated deguelin derivatives as heat shock protein 90 (HSP90) inhibitors
Kim, Ho Shin,Hong, Mannkyu,Ann, Jihyae,Yoon, Suyoung,Nguyen, Cong-Truong,Lee, Su-Chan,Lee, Ho-Young,Suh, Young-Ger,Seo, Ji Hae,Choi, Hoon,Kim, Jun Yong,Kim, Kyu-Won,Kim, Joohwan,Kim, Young-Myeong,Park, So-Jung,Park, Hyun-Ju,Lee, Jeewoo
, p. 6082 - 6093 (2016/11/09)
Based on the lead compound L-80 (compound 2), a potent heat shock protein 90 (HSP90) inhibitor, a series of C-ring truncated deguelin analogs were designed, synthesized and evaluated for Hypoxia Inducible Factor-1α (HIF-1α) inhibition as a primary screening method. Their structure–activity relationship was investigated in a systematic manner by varying the A/B ring, linker and D/E ring, respectively. Among the synthesized inhibitors, compound 5 exhibited potent HIF-1α inhibition in a dose-dependent manner and significant antitumor activity in human non-small cell lung carcinoma (H1299), with better activities than L-80. It also inhibited in vitro hypoxia-mediated angiogenic processes in human retinal microvascular endothelial cells (HRMEC). The docking study of 5 showed a similar binding mode as L-80: it occupied the C-terminal ATP-binding pocket of HSP90, indicating that the anticancer and antiangiogenic activities of 5 were derived from HIF-1α destabilization by inhibiting the C-terminal ATP-binding site of hHSP90.
Straightforward synthesis of 2-propylquinolines under multicomponent conditions in fluorinated alcohols
Venkateswarlu,Balaji,De, Kavita,Crousse, Benoit,Figadère, Bruno,Legros, Julien
, p. 94 - 98 (2013/11/06)
The synthesis of 2-propylquinolines, a family of antileishmanial agents, is reported. Among the pathways explored, the 3-component Povarov reaction between butyraldehyde, aromatic amines and ethyl vinyl ether in trifluoroethanol (TFE), followed by an oxidation, offers a convenient entry to 2-propylquinolines with various substituents on positions 5-8.
Heteroannulation of 3-Bis(methylthio)acrolein with Aromatic Amines - A Convenient Highly Regioselective Synthesis of 2-(Methylthio)quinolines and their Benzo/Hetero Fused Analogs: A Modified Skraup Quinoline Synthesis
Panda, Kausik,Siddiqui, Iffat,Mahata, Pranab K.,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
, p. 449 - 452 (2007/10/03)
A simple and efficient synthesis of 2-(methylthio)quinolines and their condensed analogs has been developed through acid-induced cyclocondensation of their respective anilines or aromatic diamines with 3-bis(methylthio)acrolein. The 2-(methylthio) functionality in these quinolines could be either dethiomethylated or replaced by various nitrogen and carbon nucleophiles to afford 2-substituted quinolines.
A practical route to quinolines from anilines
Tokuyama, Hidetoshi,Sato, Masashi,Ueda, Toshihiro,Fukuyama, Tohru
, p. 105 - 108 (2007/10/03)
A practical route to quinoline from anilines through acid-mediated cyclization of 3-(N-aryl-N-sulfonylamino)propionaldehydes has been developed. Treatment of the cyclization products, dihydroquinoline intermediates with KOH in DMSO leads to substituted quinolines.
Preparation of Quinone Imine Ketals via Intramolecular Condensation of Amino-Substituted Quinone Monoketals. Anodic Oxidation Chemistry of Trifluoracetamide Derivatives of 1,4-Dimethoxybenzenes and 4-Methoxyphenols
Swenton, John S.,Shih, Chuan,Chen, Chung-Pin,Chou, Chun-Tzer
, p. 2019 - 2026 (2007/10/02)
Two routes have been developed to the previously unknown quinone imine ketal moiety.One involves a sequence of anodic oxidation of the N-trifluoroacetamide of a 2-(2,5-dimethoxyphenyl)ethylamine or 3-(2,5-dimethoxyphenyl)propylamine derivative to form the respective quinone bisketal followed by basic hydrolysis of the trifluoroacetamide linkage, acidic hydrolysis of the quinone bisketal to a quinone monoketal, and intramolecular condensation to form the quinone imine ketal.This method reuires an additional substituent at the 4-position (bromine or methoxy) to direct the regiochemistry of the quinone bisketal hydrolysis.The second method involves similar chemistry except that the anodic oxidation of a 4-methoxyphenol derivative directly affords the quinone monoketal.Hydrolysis of the trifluoroacetamide followed by an intramolecular condensation reaction affords the quinone imine ketal.Selected aspects of the chemistry of these compounds have been studied.Especially interesting is the reaction of a model quinone imine ketal with organolithium reagents.Either 1- or 2-substituted-5-methoxyindole is produced, depending upon the organolithium compound.
A GENERAL APPROACH TO QUINONE IMINE KETALS. INTERESTING INTERMEDIATES FOR PREPARATION OF 5-OXYGENATED INDOLES AND QUINONE IMINES
Chen, Chung-Pin,Shih, Chuan,Swenton, John S.
, p. 1891 - 1894 (2007/10/02)
A general route for the preparation of quinone imine ketals is reported.
