Literature DB >> 17188868

Structural simplification of bioactive natural products with multicomponent synthesis: dihydropyridopyrazole analogues of podophyllotoxin.

Igor V Magedov1, Madhuri Manpadi, Elena Rozhkova, Nikolai M Przheval'skii, Snezna Rogelj, Scott T Shors, Wim F A Steelant, Severine Van slambrouck, Alexander Kornienko.   

Abstract

A three-component condensation of 5-amino-3-methylpyrazole, tetronic acid, and various aromatic, heteroaromatic, and aliphatic aldehydes leads to the formation of dihydropyridopyrazole analogues of a cytotoxic lignan podophyllotoxin. This new heterocyclic scaffold-based library allows a drastic reduction of the structural complexity of the natural product with the retention of its potent cytotoxic properties. Similarly to podophyllotoxin, the presented analogues induce apoptosis in Jurkat cells.

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Year:  2006        PMID： 17188868      PMCID： PMC3393043          DOI： 10.1016/j.bmcl.2006.11.095

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  11 in total

1.  Structure-Activity studies for a novel series of tricyclic dihydropyrimidines as K(ATP) channel openers (KCOs).

Authors:  Irene Drizin; Mark W Holladay; Lin Yi; Henry Q Zhang; Sujatha Gopalakrishnan; Murali Gopalakrishnan; Kristi L Whiteaker; Steven A Buckner; James P Sullivan; William A Carroll
Journal:  Bioorg Med Chem Lett       Date:  2002-06-03       Impact factor: 2.823

2.  Synthesis and cytotoxic evaluation of combretafurans, potential scaffolds for dual-action antitumoral agents.

Authors:  Tracey Pirali; Sara Busacca; Lorena Beltrami; Daniela Imovilli; Francesca Pagliai; Gianluca Miglio; Alberto Massarotti; Luisella Verotta; Gian Cesare Tron; Giovanni Sorba; Armando A Genazzani
Journal:  J Med Chem       Date:  2006-08-24       Impact factor: 7.446

3.  Estrogen receptor beta-subtype selective tetrahydrofluorenones: use of a fused pyrazole as a phenol bioisostere.

Authors:  R R Wilkening; R W Ratcliffe; A K Fried; D Meng; W Sun; L Colwell; S Lambert; M Greenlee; S Nilsson; A Thorsell; M Mojena; C Tudela; K Frisch; W Chan; E T Birzin; S P Rohrer; M L Hammond
Journal:  Bioorg Med Chem Lett       Date:  2006-05-30       Impact factor: 2.823

Review 4.  Antitumor properties of podophyllotoxin and related compounds.

Authors:  M Gordaliza; M A Castro; J M del Corral; A S Feliciano
Journal:  Curr Pharm Des       Date:  2000-12       Impact factor: 3.116

5.  Nonenolizable podophyllotoxin derivatives.

Authors:  W J Gensler; C D Murthy; M H Trammell
Journal:  J Med Chem       Date:  1977-05       Impact factor: 7.446

6.  Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.

Authors:  T Mosmann
Journal:  J Immunol Methods       Date:  1983-12-16       Impact factor: 2.303

7.  Subtype-selective N-methyl-D-aspartate receptor antagonists: synthesis and biological evaluation of 1-(heteroarylalkynyl)-4-benzylpiperidines.

Authors:  J L Wright; T F Gregory; S R Kesten; P A Boxer; K A Serpa; L T Meltzer; L D Wise; S A Espitia; C S Konkoy; E R Whittemore; R M Woodward
Journal:  J Med Chem       Date:  2000-09-07       Impact factor: 7.446

8.  4-Aza-2,3-dehydro-4-deoxypodophyllotoxins: simple aza-podophyllotoxin analogues possessing potent cytotoxicity.

Authors:  Y Hitotsuyanagi; M Fukuyo; K Tsuda; M Kobayashi; A Ozeki; H Itokawa; K Takeya
Journal:  Bioorg Med Chem Lett       Date:  2000-02-21       Impact factor: 2.823

Review 9.  Podophyllotoxin derivatives: current synthetic approaches for new anticancer agents.

Authors:  Youngjae You
Journal:  Curr Pharm Des       Date:  2005       Impact factor: 3.116

10.  Discovery of podophyllotoxins.

Authors:  T F Imbert
Journal:  Biochimie       Date:  1998-03       Impact factor: 4.079
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  11 in total

1.  Multicomponent Synthesis of 2,3-Dihydrochromeno[4,3-d]pyrazolo[3,4-b]pyridine-1,6-diones: A Novel Heterocyclic Scaffold with Antibacterial Activity.

Authors:  Liliya V Frolova; Indranil Malik; Pavel Y Uglinskii; Snezna Rogelj; Alexander Kornienko; Igor V Magedov
Journal:  Tetrahedron Lett       Date:  2011-12-07       Impact factor: 2.415

Review 2.  Natural products as leads to anticancer drugs.

Authors:  M Gordaliza
Journal:  Clin Transl Oncol       Date:  2007-12       Impact factor: 3.405

3.  Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-pyrano-[2,3-b]naphthoquinones with anticancer activity.

Authors:  Igor V Magedov; Artem S Kireev; Aaron R Jenkins; Nikolai M Evdokimov; Dustin T Lima; Paul Tongwa; Jeff Altig; Wim F A Steelant; Severine Van slambrouck; Mikhail Yu Antipin; Alexander Kornienko
Journal:  Bioorg Med Chem Lett       Date:  2012-07-04       Impact factor: 2.823

4.  Anticancer properties of an important drug lead podophyllotoxin can be efficiently mimicked by diverse heterocyclic scaffolds accessible via one-step synthesis.

Authors:  Igor V Magedov; Liliya Frolova; Madhuri Manpadi; Uma devi Bhoga; Hong Tang; Nikolai M Evdokimov; Olivia George; Kathy Hadje Georgiou; Steffen Renner; Matthäus Getlik; Tiffany L Kinnibrugh; Manuel A Fernandes; Severine Van slambrouck; Wim F A Steelant; Charles B Shuster; Snezna Rogelj; Willem A L van Otterlo; Alexander Kornienko
Journal:  J Med Chem       Date:  2011-05-26       Impact factor: 7.446

Review 5.  Advancements in tetronic acid chemistry. Part 2: Use as a simple precursor to privileged heterocyclic motifs.

Authors:  Moaz M Abdou; Rasha A El-Saeed; Khaled M Elattar; Zeynel Seferoğlu; John Boukouvalas
Journal:  Mol Divers       Date:  2016-06-27       Impact factor: 2.943

6.  Structural simplification of bioactive natural products with multicomponent synthesis. 3. Fused uracil-containing heterocycles as novel topoisomerase-targeting agents.

Authors:  Nikolai M Evdokimov; Severine Van Slambrouck; Petra Heffeter; Lee Tu; Benjamin Le Calvé; Delphine Lamoral-Theys; Carla J Hooten; Pavel Y Uglinskii; Snezna Rogelj; Robert Kiss; Wim F A Steelant; Walter Berger; Jeremy J Yang; Cristian G Bologa; Alexander Kornienko; Igor V Magedov
Journal:  J Med Chem       Date:  2011-03-09       Impact factor: 7.446

7.  7-p-Tolyl-10,11-dihydro-benzo[h]furo[3,4-b]quinolin-8(7H)-one.

Authors:  Chunling Shi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-02-20

8.  Structural simplification of bioactive natural products with multicomponent synthesis. 2. antiproliferative and antitubulin activities of pyrano[3,2-c]pyridones and pyrano[3,2-c]quinolones.

Authors:  Igor V Magedov; Madhuri Manpadi; Marcia A Ogasawara; Adriana S Dhawan; Snezna Rogelj; Severine Van Slambrouck; Wim F A Steelant; Nikolai M Evdokimov; Pavel Y Uglinskii; Eerik M Elias; Erica J Knee; Paul Tongwa; Mikhail Yu Antipin; Alexander Kornienko
Journal:  J Med Chem       Date:  2008-03-25       Impact factor: 7.446

9.  Small Molecule Compounds That Inhibit Antioxidant Response Gene Expression in an Inducer-Dependent Manner.

Authors:  Megan R Edwards; Gai Liu; Sampriti De; Julien Sourimant; Colette Pietzsch; Britney Johnson; Gaya K Amarasinghe; Daisy W Leung; Alexander Bukreyev; Richard K Plemper; Zachary Aron; Terry L Bowlin; Donald T Moir; Christopher F Basler
Journal:  ACS Infect Dis       Date:  2020-01-15       Impact factor: 5.084

10.  7-Methyl-9-p-tolyl-4,9-dihydro-furo[3,4-b]quinolin-1(3H)-one.

Authors:  Chunling Shi; Min Ji
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-12-13
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