Elaborating on Efficient Anti‐Proliferation Agents of Cancer Cells and Anti‐Inflammatory‐Based <i>N</i>‐Bisphosphonic Acids

Abdou, Wafaa M.; Khidre, Rizk E.; Kamel, Azza A.

doi:10.1002/ardp.201100080

Cited by 37 publications

(22 citation statements)

References 32 publications

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“…Eight of ten tested compounds exhibited remarkable anti-tumor activity against breast, and prostate cancer, and a promised anti-tumor sensitivity toward ovarian cancer and melanoma. Conversely, there was only scattered activity against leukemia; and no noticeable action of these BP-acids on CNS or lung cancer [66,67].…”

Section: Synthesis Of Some Anti-tumor Bp-compoundsmentioning

confidence: 98%

Gem-Diphosphonates: The Motif of Diverse Biological and Medicinal Importance

Abdou¹,

Barghash²

2015

JPP

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Section: Synthesis Of Some Anti-tumor Bp-compoundsmentioning

confidence: 98%

Gem-Diphosphonates: The Motif of Diverse Biological and Medicinal Importance

Abdou¹,

Barghash²

2015

JPP

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“…[2] A perusal of literature shows that interesting pharmacological properties have been associated with 2-chloroquinoline-3-carbaldehydes and their derivatives. [3,4] These compounds have shown antimicrobial, [1][2][3] antimalarial, [5,6] anti-inflammatory, [7][8][9][10] antitumor, [11,12] and antiparasitic activity. [13] A recent review by Wahab et al [13] summarized and provided an excellent bibliography on the synthetic methods, reactions, and biological applications of 2-chloroquinoline-3-carbaldehydes during the period from 1999 to 2011.…”

Section: Introductionmentioning

confidence: 99%

Kinetic and Mechanistic Study of Transition Metal Ion Catalyzed Vilsmeier–Haack Cyclization and Formylation Reactions with Acetanilides

Aneesa

Rajanna

Reddy

et al. 2015

Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-

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Vilsmeier-Haack reactions (VHR) with acetanilides afforded 2-chloro 3-formyl quinoline derivatives. The reactions obeyed second order kinetics with a first order dependence on VHR as well as acetanilide. Significant rate enhancements were observed when transition metal ions such as Cu(II), Ni(II), Co(II), and Cd(II) were used as catalysts in these reactions. The kinetic results in transition metal ion catalyzed reactions coupled with uv-visible spectrophotometric observations substantiated the participation of mixed ligand precursors of the type [M(II)S(VHR)] involving acetanilides and VH reagents in the rate limiting step. Activation parameters were computed and interpreted suitably.

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“…1,2 These compounds have shown antimicrobial, [1][2][3] antimalarial, 4,5 anti-inflammatory, [6][7][8][9] antitumor, 10,11 and anti-parasitic activity. 12 Despite this versatile importance, and in connection to our previous review articles about biologically active heterocyclic systems, 13 2-chloroquinoline-3-carbaldehydes have not been previously reviewed.…”

Section: Introductionmentioning

confidence: 99%

“…Condensations of aldehydes 2 or 55 with aryl (heterocycles) methyl ketones either by using microwaves under solvent-free conditions or by using conventional methods, to give quinoline chalcones 116 was reported. [10][11][12][13][14][15][16][17][18][81][82][83][84][85][86][87][88] Michael addition of tetraethyl methylenebisphosphonate to compounds 116 (R = Cl, N 3 , R 1 = Ph, thienyl, furyl, pyrryl) in EtOH/EtONa at refluxing temperature gave bisphosphonate adduct 117 (Scheme 41). …”

mentioning

confidence: 99%

2-Chloroquinoline-3-carbaldehydes: synthesis, reactions and applications

Abdel‐Wahab¹,

Khidre²,

Farahat³

et al. 2012

Arkivoc

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This review summarizes the synthetic methods, reactions and biological applications of 2-chloroquinoline-3-carbaldehydes during the period from 1999 to 2011. The reactions are subdivided in groups that cover reactions at the chloro or aldehyde substituent and reactions which involve both groups. Most reaction types have been successfully applied and used in the production of biological active compounds.Keywords: Vilsmeier-Haack reaction, quinolines, aldehydes IntroductionInteresting pharmacological properties have been associated with 2-chloroquinoline-3-carbaldehydes and their derivatives.1,2 These compounds have shown antimicrobial, [1][2][3] antimalarial, 4,5 anti-inflammatory, 6-9 antitumor, 10,11 and anti-parasitic activity. 12 Despite this versatile importance, and in connection to our previous review articles about biologically active heterocyclic systems, 13 2-chloroquinoline-3-carbaldehydes have not been previously reviewed.The main objective of the present survey is to provide the synthesis, reactions, and biological applications of 2-chloroquinoline-3-carbaldehydes from 1999 to the end of 2011 and provide useful and up-to-date data for organic and medicinal chemists. Synthetic MethodsThere have been a number of practically important routes to synthesise of 2-chloroquinoline-3-carbaldehydes, e.g. (i) Vilsmeier-Haack reaction of acetanilides, (ii) oxidation of the corresponding alcohols. Vilsmeier-Haack reaction2-Chloroquinoline-3-carbaldehydes 2 were synthesized from acetanilides 1 via a VilsmeierHaack reaction either by traditional methods [14][15][16][17][18][19][20][21][22][23] or by microwave, 24 or ultrasonic irradiation (Scheme 1). 25Scheme 1 Reviews and Accounts ARKIVOC 2012 (i) 211-276Page 213 © ARKAT-USA, Inc. Oxidation of the corresponding alcohols(2-Chloroquinolin-3-yl)methanol 3 was oxidized to aldehyde 2 using a combination of diethyl diazene-1,2-dicarboxylate (DEAD) and catalytic ZnBr 2 in refluxing toluene (Scheme 2). 26Scheme 2 3 Chemical Reactions Substitution reactionsTreatment of 2-chloroquinoline-3-carbaldehydes 2 with prenyl thiolate or prenyl alcoholate 4 in the presence of sodium hydroxide or potassium t-butoxide, furnished S/O-prenyl aldehydes 5 in 72-84% yield, respectively. S/O-prenyl aldehyde 5, underwent imino Diels-Alder reactions with various substituted anilines in the presence of InCl 3 in acetonitrile resulting in the formation mixture of cis and trans products 7 and 8 in 55-71% yields by intramolecular cycloaddition reaction of the imine 6 generated in situ in the one pot-reaction (Scheme 3). 14 Scheme 3Knoevenagel hetero Diels-Alder reaction of 5 (X = O) with N,N'-dimethylbarbituric acid in water was carried out in the presence of piperidine at room temperature. The intermediate Knoevenagel adduct 9 was not isolated and allowed to cyclise at room temperature after 3 h stirring gave the cis-fused pentacyclic pyrano [2,3-b]quinoline derivatives 10 with high yield (80%) and diastereoselectivity (> 99%) (Scheme 4). 27 Scheme 4Recently, tetrahydrocyclopenta[c]acri...

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Elaborating on Efficient Anti‐Proliferation Agents of Cancer Cells and Anti‐Inflammatory‐Based N‐Bisphosphonic Acids

Cited by 37 publications

References 32 publications

Gem-Diphosphonates: The Motif of Diverse Biological and Medicinal Importance

Gem-Diphosphonates: The Motif of Diverse Biological and Medicinal Importance

Kinetic and Mechanistic Study of Transition Metal Ion Catalyzed Vilsmeier–Haack Cyclization and Formylation Reactions with Acetanilides

2-Chloroquinoline-3-carbaldehydes: synthesis, reactions and applications

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