- 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.
-
-
- Cp*Rh(III)-Catalyzed Directed C?H Methylation and Arylation of Quinoline N-Oxides at the C-8 Position
-
Herein, we report a Cp*Rh(III)-catalyzed directed C?H methylation of quinoline N-oxides at the C-8 position using commercially available organotrifluoroborates as reagents. This method features perfect regioselectivity, relatively mild reaction conditions, and diverse functional group tolerance with good to excellent yields. Additionally, direct C-8 arylated quinoline N-oxides products could also be obtained under the same conditions. Preliminary mechanistic experiments were conducted and a possible mechanism was proposed. (Figure presented.).
- Wang, Bao,Li, Chunpu,Liu, Hong
-
supporting information
p. 3029 - 3034
(2017/09/09)
-
- Quinolines synthesis by reacting 1,3-butanediol with anilines in the presence of iron catalysts
-
2-, 4-, 6-, 7-, and 8-substituted quinolines were synthesized in 78–95% yield by the reaction of 1,3- butanediol with anilines in the presence of iron catalysts in carbon tetrachloride.
- Khusnutdinov,Bayguzina,Aminov
-
p. 1613 - 1618
(2016/08/26)
-
- 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 6
(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)
-
- 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)
-
- Addition of propargyltrimethylsilane to N-methyleneamine equivalents: Generation and electrophilic cyclization of vinylic carbocations
-
Lewis acid induced N-methyleneamine equivalents from N-(methoxymethyl)anilines or 1,3,5-triphenylhexahydro-1,3,5-triazines reacted with propargyltrimethylsilanes to give N-buta-2,3-dienylanilines, 4-methylene-1,2,3,4-tetrahydroquinolines and its oxidized product of 4-methylquinolines. These products came from branching reactions of the elimination and electrophilic aromatic substitution from the same vinylic carbocation intermediate.
- Ha, Hyun-Joon,Lee, Young-Scong,Ahn, Young-Gil
-
p. 2357 - 2364
(2007/10/03)
-