- Synthesis and antileishmanial evaluation of thiazole orange analogs
-
Cyanine compounds have previously shown excellent in vitro and promising in vivo antileishmanial efficacy, but the potential toxicity of these agents is a concern. A series of 22 analogs of thiazole orange ((Z)-1-methyl-4-((3-methylbenzo[d]thiazol-2(3H)-ylidene)methyl)quinolin-1-ium salt), a commercial cyanine dye with antileishmanial activity, were synthesized in an effort to increase the selectivity of such compounds while maintaining efficacy. Cyanines possessing substitutions on the quinolinium ring system displayed potency against Leishmania donovani axenic amastigotes that differed little from the parent compound (IC50 12–42 nM), while ring disjunction analogs were both less potent and less toxic. Changes in DNA melting temperature were modest when synthetic oligonucleotides were incubated with selected analogs (ΔTm ≤ 5 °C), with ring disjunction analogs showing the least effect on this parameter. Despite the high antileishmanial potency of the target compounds, their toxicity and relatively flat SAR suggests that further information regarding the target(s) of these molecules is needed to aid their development as antileishmanials.
- Abdelhameed, Ahmed,Liao, Xiaoping,McElroy, Craig A.,Joice, April C.,Rakotondraibe, Liva,Li, Junan,Slebodnick, Carla,Guo, Pu,Wilson, W. David,Werbovetz, Karl A.
-
supporting information
(2019/11/28)
-
- Direct access of the chiral quinolinyl core of cinchona alkaloids via a br?nsted acid and chiral amine co-catalyzed chemo- and enantioselective α-alkylation of quinolinylmethanols with enals
-
A strategy for the facile construction of the chiral quinolinylmethanolic structure, a core featured in cinchona alkaloids, is reported. A new reactivity is harnessed by TfOH-promoted chemoselective activation of α-C-H over O-H bond in quinolinylmethanols. The new reactivity is successfully engineered with an iminium catalysis in a synergistic manner to create a powerful conjugate addition-cyclization cascade process for synthesis of chiral quinoline derived π-butyrolactones in good yields and with good to excellent enantioselectivities. The method enables the first total synthesis of natural product broussonetine in three steps.
- Tong, Mengchao,Wang, Sinan,Zhuang, Jinchen,Qin, Cong,Li, Hao,Wang, Wei
-
supporting information
p. 1195 - 1199
(2018/02/23)
-
- MULTIFUNCTIONAL QUINOLINE DERIVATIVES AS ANTI-NEURODEGENERATIVE AGENTS
-
Novel quinoline derivatives are disclosed. Also disclosed are synthesis and use thereof for treating neurodegenerative diseases.
- -
-
Page/Page column 52
(2017/02/28)
-
- MULTIFUNCTIONAL QUINOLINE DERIVATIVES AS ANTI-NEURODEGENERATIVE AGENTS
-
Novel quinoline derivatives are disclosed. Also disclosed are synthesis and use thereof for treating neurodegenerative diseases.
- -
-
Paragraph 0246 - 0248
(2014/10/16)
-
- MULTIFUNCTIONAL QUINOLINE DERIVATIVES AS ANTI-NEURODEGENERATIVE AGENTS
-
Novel quinolone derivatives are disclosed. Also disclosed are synthesis and use thereof for treating neurodegenerative diseases. In an aspect, the invention relates to a composition comprising a therapeutically effective amount of the compound as aforemen
- -
-
Page/Page column 34
(2014/10/18)
-
- AROYLQUINOLINE COMPOUNDS
-
A serious of nitro heterocyclic derivatives including a structure of formula (I) are provided. In formula (I), P, Q and R1 to R8 are defined in the specification. The derivatives disclosed in the present invention are characterized in inhibiting tubulin p
- -
-
Page/Page column 12
(2011/11/13)
-
- 5-Amino-2-Aroylquinolines as highly potent tubulin polymerization inhibitors
-
A series of aroylquinoline derivatives were synthesized and evaluated for anticancer activity. 5-Amino6-methoxy-2-aroylquinoline 15 showed more potent antiproliferative activity (IC50 values ranging from 0.2 to 0.4 nM) as compared to la (combretastatin A-4) (IC50 = 1-9-835 nM) against various human cancer cell lines and a MDR-resistant cancer cell line. Compound 15 (IC50 = 1-6 μM) exhibited more potent inhibition of tubulin polymerization than la (IC50 = 2.1 μM) and showed strong binding property to the colchicine binding site of microtubules.
- Nien, Chih-Ying,Chen, Yun-Ching,Kuo, Ching-Chuan,Hsieh, Hsing-Pang,Chang, Chi-Yen,Wu, Jian-Sung,Wu, Su-Ying,Liou, Jing-Ping,Chang, Jang-Yang
-
supporting information; experimental part
p. 2309 - 2313
(2010/08/07)
-
- New nonsymmetric phenanthrolines as very effective ligands in the palladium-catalyzed carbonylation of nitrobenzene
-
Inspired by the results of a previous mechanistic study, a series of mostly new nonsymmetric phenanthrolines were synthesized and tested as ligands in the palladium-catalyzed reductive carbonylation reaction of nitrobenzene to methyl phenylcarbamate. Very good results were obtained when the asymmetry was of an electronic nature (a donating substituent in the para position of one of the two pyridinic rings and an electron-withdrawing or no substituent on the para position of the other pyridinic ring), but steric hindrance in the ortho or meta position retarded the reaction. The TOF for the modified system is the highest ever reported for any carbonylation reaction of nitroarenes.
- Ferretti, Francesco,Ragaini, Fabio,Lariccia, Roberta,Gallo, Emma,Cenini, Sergio
-
scheme or table
p. 1465 - 1471
(2010/05/15)
-
- AN IMPROVED PROCESS FOR THE SYNTHESIS OF QUINOLINE DERIVATIVES
-
The present invention provides an improved process for the synthesis of quinoline derivatives. More particularly the present invention provides an improved and economical process for the synthesis of quinoline derivatives by the reaction of aniline/substituted anilines using two different catalysts, ferric chloride and zinc chloride in a one-pot set up reaction.
- -
-
Page/Page column 5
(2008/06/13)
-
- Process for the synthesis of quinoline derivatives
-
The present invention provides an improved process for the synthesis of quinoline derivatives. More particularly the present invention provides an improved and economical process for the synthesis of quinoline derivatives by the reaction of aniline/substituted anilines using two different catalysts, ferric chloride and zinc chloride in a one-pot set up reaction.
- -
-
Page/Page column 2
(2010/11/27)
-
- High-yielding microwave assisted synthesis of quinoline and dihydroquinoline derivatives under solvent-free conditions
-
A mild and efficient solvent-free method has been developed by two different approaches for the synthesis of quinoline and dihydroquinoline derivatives: (i) one-pot reaction of anilines with alkyl vinyl ketones (Skraup reaction) (ii) between various acetophenones and 2-aminoacetophenone (Friedlaender reaction) using stable and effective heterogeneous catalyst potassium dodecatangestocobaltate (25 mol %) (PDTC) under microwave irradiation in high yields.
- Bose, D. Subhas,Kumar, Racherla Kishore
-
p. 549 - 559
(2007/10/03)
-
- Aza-and polyaza-naphthalenly ketones useful as hiv integrase inhibitors
-
Certain aza- and polyaza-naphthalenyl ketones including certain quinolinyl and naphthyridinyl ketones are described as inhibitors of HIV integrase and inhibitors of HIV replication. These compounds are useful in the prevention or treatment of infection by HIV and the treatment or the delay in the onset of AIDS, as compounds or pharmaceutically acceptable salts, or as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating or delaying the onset of AIDS and methods of preventing or treating infection by HIV are also described.
- -
-
Page/Page column 41
(2010/02/10)
-
- Efficient microwave-assisted synthesis of quinolines and dihydroquinolines under solvent-free conditions
-
A convenient and efficient procedure for the synthesis of quinolines and dihydroquinolines has been developed by a simple one-pot reaction of anilines with alkyl vinyl ketones on the surface of silica gel impregnated with indium(III) chloride under microwave irradiation without any solvent.
- Ranu, Brindaban C.,Hajra, Alakananda,Dey, Suvendu S.,Jana, Umasish
-
p. 813 - 819
(2007/10/03)
-
- Microwave-assisted simple synthesis of quinolines from anilines and alkyl vinyl ketones on the surface of silica gel in the presence of indium(III) chloride
-
A simple and efficient procedure has been developed for the synthesis of 4-alkylquinolines by a one-pot reaction of anilines with alkyl vinyl ketones on the surface of silica gel impregnated with indium(III) chloride under microwave irradiation without any solvent.
- Ranu, Brindaban C.,Hajra, Alakananda,Jana, Umasish
-
p. 531 - 533
(2007/10/03)
-
- 2,4-Diamino-5-benzylpyrimidines and analogues as antibacterial agents. 10. 2,4-Diamino-5-(6-quinolylmethyl)- and -[(tetrahydro-6-quinolyl)methyl]pyrimidine derivatives. Further specificity studies
-
A series of 18 2,4-diamino-5-[(1,2,3,4-tetrahydro-6-quinolyl)methyl]pyrimidines has been prepared by the condensation of 2,4-diamino-5-(hydroxymethyl)pyrimidine with 1,2,3,4-tetrahydroquinolines in acidic medium. Several derivatives were catalytically aromatized; others were synthesized from these by routine aromatic substitution or by condensations of (anilinomethyl)pyrimidines to give quinolinylmethyl analogues. Compounds with 4-methyl-8-methoxy substitution are closely related to trimethoprim (1a) in structure and are excellent inhibitors of bacterial dihydrofolate reductase, with activity at least equivalent to that of 1a. The highest degree of inhibition was achieved with the rigid aromatic series, but greater specificity was accomplished among the tetrahydroquinoline derivatives. This was directly related to N-1 substitution of 4-methyl-8-methoxy derivatives. The spatial relationships around N-1 and protonation at this site may both affect selectivity. Such compounds also had excellent broad-spectrum in vitro antibacterial activity.
- Rauckman,Tidwell,Johnson,Roth
-
p. 1927 - 1935
(2007/10/02)
-
- 2,4-diamino-5-(1,2,3,4-tetrahydro-(substituted or unsubstituted)-6-quinolylmethyl)pyrimidines, useful as antimicrobials
-
Compounds of the formula (II) STR1 or a salt, N-oxide or acyl derivative thereof, wherein Y is a group STR2 which is optionaly substituted and which optionally contain a nitrogen atom at one of positions A, B, C, D or E, in which the dotted line represents aromatic rings unless one of the rings contains a nitrogen atom in which case this ring is either aromatic or partially saturated, have antimicrobial properties. Processes for making these compounds, pharmaceutical compositions containing them and the medical use of the compounds are also disclosed.
- -
-
-