cas 82121-05-9, 7-Methoxy-4-quinolinol | Articles data

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Design, synthesis, structure-activity relationships and mechanism of action of new quinoline derivatives as potential antitumor agents
A series of new quinoline derivatives was designed, synthesized and evaluated as potential antitumor agents. The results indicated that most compounds exhibited potent antiproliferative activity, and 7-(4-fluorobenzyloxy)–N-(2-(dimethylamino)- ethyl)quinolin-4-amine 10g was found to be the most potent antiproliferative agent against human tumor cell lines with an IC50 value of less than 1.0 μM. Preliminary structure-activity relationships analysis suggested that (1) the large and bulky alkoxy substituent in position-7 might be a beneficial pharmacophoric group for antiproliferative activity; (2) the amino side chain substituents in position-4 facilitated the antiproliferative activity of this class of compounds; and (3) the length of the alkylamino side chain moiety affected the antiproliferative potency, with two CH2 units being the most favorable. Further investigation of the mechanism of action of this class of compounds demonstrated that the representative compound 10g triggered p53/Bax-dependent colorectal cancer cell apoptosis by activating p53 transcriptional activity. Moreover, the results showed that compound 10g effectively inhibited tumor growth in a colorectal cancer xenograft model in nude mice. Thus, these quinoline derivatives might serve as candidates for the development of new antitumor drugs.
Li, Shangze,Hu, Lihua,Li, Jianru,Zhu, Jiongchang,Zeng, Feng,Huang, Qiuhua,Qiu, Liqin,Du, Runlei,Cao, Rihui
p. 666 - 678
(2018/11/30)

Design, synthesis and biological evaluation of new quinoline derivatives as potential antitumor agents
A series of new quinoline derivatives was designed, synthesized and evaluated for their antiproliferative activity. The results demonstrated that compounds 11p, 11s, 11v, 11x and 11y exhibited potent antiproliferative activity with IC50 value of lower than 10 μM against seven human tumor cell lines, and N-(3-methoxyphenyl)-7- (3-phenylpropoxy)quinolin-4-amine 11x was found to be the most potent antiproliferative agent against HCT-116, RKO, A2780 and Hela cell lines with an IC50 value of 2.56, 3.67, 3.46 and 2.71 μM, respectively. The antitumor efficacy of the representative compound 11x in mice was also evaluated, and the results showed that compound 11x effectively inhibited tumor growth and decreased tumor weight in animal models. Further investigation on mechanism of action indicated that compound 11x could inhibit colorectal cancer growth through ATG5-depenent autophagy pathway. Therefore, these quinoline derivatives are a new class of molecules that have the potential to be developed as new antitumor drugs.
Su, Tong,Zhu, Jiongchang,Sun, Rongqin,Zhang, Huihui,Huang, Qiuhua,Zhang, Xiaodong,Du, Runlei,Qiu, Liqin,Cao, Rihui
p. 154 - 167
(2019/06/11)

PROCESS FOR PREPARING SUBSTITUTED QUINOLIN-4-OL COMPOUNDS
The invention relates to a process for preparing substituted quinolin-4-ol compounds useful for preparing protein tyrosine kinase (PTK) inhibitors which are useful in treating cancer.
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Paragraph 0087

(2018/03/01)

Substituted 4 - hydroxy quinoline compound of preparation method (by machine translation)
The invention relates to substituted 4 - hydroxy quinoline compound of preparation method, the compounds are used for preparing the protein tyrosine kinase for the treatment of cancer (PTK) inhibitors of intermediate. (by machine translation)
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Paragraph 0161-0163; 0166-0171; 0175; 0176

(2018/04/02)

For antibacterial chlorine oxygen kui derivatives
The invention relates to an oxo-quinoline derivative with activity of resisting bacterial infection relevant diseases such as helicobacter pylori (Hp) infection disease. The invention specifically relates to a compound as shown in formula I in the specification, and a pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R is selected from hydrogen, -C alkyl, -C alkenyl, -C alkynyl, or -C alkyl-phenyl, and the alkyl, alkenyl, alkynyl and phenyl can be randomly substituted by halogen, nitro, cyan, hydroxyl, -C alkoxy and phenyl; R is selected from hydrogen, -CONHR and -COOR, R and R are independently selected from -C alkyl and -C alkyl amino, and the amino is randomly substituted by one to two -C alkyls; R is selected from halogen, -C alkoxy, morpholinyl or piperazinyl.
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Paragraph 0172-0173; 0193-0194; 0201-0202

(2017/08/29)

With anti-tumor activity of chlorine oxygen kui derivatives
The invention relates to a chloroxoquinoline derivatives with anti-tumor activity and specifically relates to compounds of a formula I as shown in the specification and pharmaceutically acceptable salts, solvates and prodrugs thereof, wherein R1 is selected from hydrogen, -C1-6 alkyl, -C2-6 alkenyl, -C2-6 alkynyl and -C1-6 alkyl-phenyl, and the alkyl, the alkenyl, the alkynyl and the phenyl can be optionally substituted by halogens, nitryl, cyan, hydroxyl, -C1-6 alkoxy and phenyl; R3 is selected from hydrogen, -CONHR31 and -COOR32, the R31 and the R32 are independently selected from -C1-6 alkyl and -C1-6 alkylamino, respectively, and the amino can be optionally substituted by 1 to 2 -C1-6 alkyls; R7 is selected from halogens, -C1-6 alkoxy, morpholinyl and piperazine; the formula I is as shown in the specification.
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Paragraph 0176; 0196; 0197; 0204; 0205

(2017/12/28)

Co(III)-Catalyzed Enaminone-Directed C-H Amidation for Quinolone Synthesis
We report herein the development of a Co(III)-catalyzed enaminone-directed C-H amidation method for synthetic access to quinolones, an important heterocyclic scaffold for diverse pharmaceutically active structures. The C-H coupling with dioxazolones and subsequent deacylation of an installed amide group allow consecutive C-N coupling generation of quinolones with wide-ranging compatible substituent patterns.
Shi, Pengfei,Wang, Lili,Chen, Kehao,Wang, Jie,Zhu, Jin
p. 2418 - 2421
(2017/05/12)

Cobalt(III)- and Rhodium(III)-Catalyzed C-H Amidation and Synthesis of 4-Quinolones: C-H Activation Assisted by Weakly Coordinating and Functionalizable Enaminone
Cobalt(III) and rhodium(III) catalysts exhibited complementary scope in C-H amidation of aryl enaminones. The amidation reactions proceeded with broad scope under the assistance of a weakly coordinating and bifunctional enaminone directing group. The electrophilicity of the enaminone group can be further utilized in subsequent hydrolysis-cyclization reactions to afford NH 4-quinolones in telescoping reactions.
Wang, Fen,Jin, Liang,Kong, Lingheng,Li, Xingwei
supporting information
p. 1812 - 1815
(2017/04/11)

Structure-activity relationships for ferriprotoporphyrin IX association and β-hematin inhibition by 4-aminoquinolines using experimental and ab initio methods
In order to probe structure-activity relationships of association with ferriprotoporphyrin IX (log K) and inhibition of β-hematin formation, a series of 4-aminoquinolines with varying substituents at the 7-position (X) have been synthesized. These have been further elaborated by introduction of two different R groups on the 4-amino nitrogen atom in the form of methyl (R = Me) and ethylamine (R = EtNH2) side chains. Data for a previously investigated series containing an N,N-diethyl-ethylamine side chain were also compared with the findings of this study. Experimentally, log K values for the simple 4-aminoquinoline series (R = H) were found to correlate with the hydrophobicity constant (π) of the group X. The log K values for the series with R = Me and EtNH2 were found to correlate with those of the series with R = H. The log of the 50% β-hematin inhibitory activity (log BHIA50) was found to correlate with log K and either meta (σm) or para (σp) Hammett constants for the series with R = Me and EtNH2, but not the simple series with R = H. To further improve predictability, correlations with ab initio electrostatic parameters, namely Mulliken and CHelpG charges were investigated. The best correlations were found with CHelpG charges which indicated that log K values can be predicted from the charges on atom H-8 and the group X in the quinolinium species computed in vacuum, while log BHIA50 values can be predicted from the CHelpG charges on C-7, C-8 and N-1 for the neutral species in vacuum. These correlations indicate that association and inhibition of β-hematin formation are separately determined. They also suggest that electron withdrawing groups at the 7-position, but not necessarily hydrophobic groups are required for hemozoin inhibition. The upshot is that the correlations imply that considerably more hydrophilic hemozoin inhibitors are feasible.
Nsumiwa, Samkele,Kuter, David,Wittlin, Sergio,Chibale, Kelly,Egan, Timothy J.
p. 3738 - 3748
(2013/07/19)

Further studies on bis-charged tetraazacyclophanes as potent inhibitors of small conductance Ca2+-activated K+ channels
Previously, quinolinium-based tetraazacyclophanes, such as UCL 1684 and UCL 1848, have been shown to be extraordinarily sensitive to changes in chemical structure (especially to the size of the cyclophane system) with respect to activity as potent non-peptidic blockers of the small conductance Ca 2+-activated K+ ion channels (SKCa). The present work has sought to optimize the structure of the linking chains in UCL 1848. We report the synthesis and SKCa channel-blocking activity of 29 analogues of UCL 1848 in which the central CH2 of UCL 1848 is replaced by other groups X or Y = O, S, CF2, CO, CHOH, CC, CHCH, CHMe to explore whether subtle changes in bond length or flexibility can improve potency still further. The possibility of improving potency by introducing ring substituents has also been explored by synthesizing and testing 25 analogues of UCL 1684 and UCL 1848 with substituents (NO2, NH2, CF 3, F, Cl, CH3, OCH3, OCF3, OH) in the 5, 6 or 7 positions of the aminoquinolinium rings. As in our earlier work, each compound was assayed for inhibition of the afterhyperpolarization (AHP) in rat sympathetic neurons, an action mediated by the SK3 subtype of the SK Ca channel. One of the new compounds (39, R7 = Cl, UCL 2053) is twice as potent as UCL 1848 and UCL 1684: seven are comparable in activity.
Yang, Donglai,Arifhodzic, Lejla,Ganellin, C. Robin,Jenkinson, Donald H.
p. 907 - 923
(2013/07/27)

Synthesis of 2,3-dihydro-4(1H)-quinolones and the corresponding 4(1H)-quinolones via low-temperature fries rearrangement of N-arylazetidin-2- ones
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).
Lange, Jens,Bissember, Alex C.,Banwell, Martin G.,Cade, Ian A.
p. 454 - 470
(2011/10/09)

Regioselective synthesis of quinolin-4-ones by pyrolysis of anilinomethylene derivatives of Meldrum's acid
Electron-rich and electron-deficient anilinomethylene derivatives of Meldrum's acid cyclize equally efficiently to quinolin-4-ones via imidoylketene intermediates under flash vacuum pyrolysis (FVP) conditions. Georg Thieme Verlag Stuttgart.
Hill, Lawrence,Imam, S. Haider,McNab, Hamish,O'Neill, William J.
experimental part
p. 1847 - 1851
(2009/12/05)

A mild, one-pot synthesis of 4-quinolones via sequential Pd-catalyzed amidation and base-promoted cyclization
(Chemical Equation Presented) A mild, one-pot synthesis of 4-quinolones is described. Under the optimal conditions, a variety of 2-substituted 4-quinolones were synthesized via sequential palladium-catalyzed amidation of 2′-bromoacetophenones followed by base-promoted intramolecular cyclization.
Huang, Jinkun,Chen, Ying,King, Anthony O.,Dilmeghani, Mina,Larsen, Robert D.,Faul, Margaret M.
supporting information; experimental part
p. 2609 - 2612
(2009/05/27)

Strategic studies in the syntheses of novel 6,7-substituted quinolones and 7- or 6-substituted 1,6- and 1,7-naphthyridones
This paper describes the different strategies devised and applied to overcome the selectivity issues in the syntheses of 6,7-disubstituted-1H-quinolin-4-one, 7-substituted-1H-1,6-naphthyridin-4-one and 6-substituted-1H-1,7-naphthyridin-4-one derivatives. They allowed us to improve the overall yields and the scaling-up feasibility. Several examples illustrate these strategies with their advantages and drawbacks.
Morgentin, Rémy,Pasquet, Georges,Boutron, Pascal,Jung, Frédéric,Lamorlette, Maryannick,Maudet, Micka?l,Plé, Patrick
p. 2772 - 2782
(2008/09/19)

Preparation of quinoline hexose analogs as novel chloroquine-resistant malaria treatments (1). Synthesis of 4-hydroxyquinoline-β-glucosides
Quinoline hexose analogs are expected to be useful as novel agents for treatment of chloroquine-resistant malaria. Here, we report preparation of 4-hydroxy quinoline-β-glucosides from anilines in 4 steps.
Suzuki, Hiroshi,Aly, Nagwa S. M.,Wataya, Yusuke,Kim, Hye-Sook,Tamai, Ikumi,Kita, Masaki,Uemura, Daisuke
p. 821 - 824
(2008/02/13)

Gas-phase pyrolysis in organic synthesis: Rapid green synthesis of 4-quinolinones
Gas-phase pyrolysis of aminomethylene Meldrum's acid derivatives gave quinolinones and/or amines depending on the nature of arylamino moiety. Effect of substituent on reaction rate and nature of pyrolysis products supports the suggested intramolecular nucleophilic substitution reaction via initially formed keteneamine intermediate. Georg Thieme Verlag Stuttgart.
Al-Awadi, Nouria A.,Abdelhamid, Ismail Abdelshafy,Al-Etaibi, Alya M.,Elnagdi, Mohamed Hilmy
p. 2205 - 2208
(2008/02/10)

COMPOUNDS FOR THE TREATMENT OF MULTI-DRUG RESISTANT BACTERIAL INFECTIONS
The present invention relates to compounds that demonstrate antibacterial activity, processes for their preparation, pharmaceutical compositions containing them as the active ingredient, to their use as medicaments and to their use in the manufacture of medicaments for use in the treatment of bacterial infections in warm-blooded animals such as humans. In particular this invention relates to compounds useful for the treatment of bacterial infections in warm-blooded animals such as humans, more particularly to the use of these compounds in the manufacture of medicaments for use in the treatment of bacterial infections in warm-blooded animals such as humans.
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Page/Page column 56

(2010/11/25)

COMPOUND HAVING TGF-BETA INHIBITORY ACTIVITY AND PHARMACEUTICAL COMPOSITION CONTAINING SAME
The present invention provides compounds of formula (I) or compounds of formula (II) and pharmaceutically acceptable salts or solvates thereof. An objective of the present invention is to provide compounds having TGF2 inhibitory activity.
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Page/Page column 46

(2010/11/24)

NAPHTHALENE CARBOXAMIDES AND THEIR DERIVATIVES USEFUL AS NEW ANTI-ANGIOGENIC AGENTS
The invention relates to compounds represented by Formula (I) and to prodrugs thereof, pharmaceutically acceptable salts or solvates of said compounds or said prodrugs, wherein each of R1a-d , R2a-b , R3, and X1 are defined herein, The invention also relates to pharmaceutical compositions containing the compounds of Formula (I) and to methods of treating hyperproliferative disorders in a mammal by administering compounds of Formula(l).
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Page/Page column 77

(2010/02/11)

NOVEL QUINOLINE DERIVATIVES
The invention relates to compounds represented by Formula (I): and to pharmaceutically acceptable salts or solvates of said compounds, wherein each of A, R3-8, X3, X5, m, and n are defined herein. The invention also relates to pharmaceutical compositions containing the compounds of Formula (I) and to methods of treating hyperproliferative disorders in a mammal by administering compounds of Formula (I).
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Page/Page column 70

(2008/06/13)

THIENOPYRIDINE-PHENYLACET AMIDES AND THEIR DERIVATIVES USEFUL AS NEW ANTI-ANGIOGENIC AGENTS
The invention relates to compounds represented by Formula (I):, and to prodrugs thereof, pharmaceutically salts or solvates of said compounds or said prodrugs, wherein each of X1-X5 and R1-R5 are defined herein. The invention also relates to pharmaceutical compositions containing the compounds of Formula (I) and to methods of treating hyperproliferative disorders in a mammal by administering compounds of Formula (I).
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Page/Page column 94-95

(2010/02/11)

HEPATITIS C VIRUS INHIBITORS
Hepatitis C virus inhibitors are disclosed having the general formula:(I) wherein R1, R2, R3, R', B, Y and X are described in the description. Compositions comprising the compounds and methods for using the compounds toinhibit HCV are also disclosed.
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Page 513-514

(2008/06/13)

Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof
Thiazolo-, oxazolo- and selenazolo[4,5-c]quinolin-4-amines and analogs thereof are described including methods of manufacture and the use of novel intermediates. The compounds are immunomodulators and induce cytokine biosynthesis, including interferon and/or tumor biosynthesis, necrosis factor, and inhibit the T-helper-type 2 immune response. The compounds are further useful in the treatment of viral and neoplastic diseases.
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(2008/06/13)

Structure-activity relationships for antiplasmodial activity among 7- substituted 4-aminoquinolines
Aminoquinolines (AQs) with diaminoalkane side chains (-HNRNEt2) shorter or longer than the isopentyl side chain [-HNCHMe(CH2)3NEt2] of chloroquine are active against both chloroquine-susceptible and -resistant Plasmodium falciparum. (De, D.; et al. Am. J. Trop. Med. Hyg. 1996, 55, 579-583). In the studies reported here, we examined structure-activity relationships (SARs) among AQs with different N,N-diethyldiaminoalkane side chains and different substituents at the 7-position occupied by Cl in chloroquine. 7-Iodo- and 7- bromo-AQs with diaminoalkane side chains [-HN(CH2)2NEt2, -HN(CH2)3NEt2, or -HNCHMeCH2NEt2] were as active as the corresponding 7-chloro-AQs against both chloroquine-susceptible and -resistant P. falciparum (IC50s of 3-12 nM). In contrast, with one exception, 7-fluoro-AQs and 7-trifluoromethyl-AQs were less active against chloroquine-susceptible P. falciparum (IC50s of 15-50 nM) and substantially less active against chloroquine-resistant P. falciparum (IC50s of 18-500 nM). Furthermore, most 7-OMe-AQs were inactive against both chloroquine-susceptible (IC50s of 17-150 nM) and -resistant P. falciparum (IC50s of 90-3000 nM).
De, Dibyendu,Krogstad, Frances M.,Byers, Larry D.,Krogstad, Donald J.
p. 4918 - 4926
(2007/10/03)

Thioquinolone compounds which have useful pharmaceutical activity
Disclosed is a thioquinolone derivative which exhibits highly selective antibacterial activity against Helicobacter pylori.
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(2008/06/13)