Literature DB >> 18450457

E,E-2-Benzylidene-6-(nitrobenzylidene)cyclohexanones: syntheses, cytotoxicity and an examination of some of their electronic, steric, and hydrophobic properties.

Umashankar Das1, Alireza Doroudi, Swagatika Das, Brian Bandy, Jan Balzarini, Erik De Clercq, Jonathan R Dimmock.   

Abstract

Three series of structurally isomeric 2-benzylidene-6-(nitrobenzylidene) cyclohexanones 1-3 were prepared and evaluated against human Molt/C8 and CEM T-lymphocytes as well as murine L1210 cells. The IC(50) values of the majority of compounds are less than 10microM and in some assays, the figures for 1d and 1e are submicromolar. Correlations were discerned between cytotoxic potencies and the atomic charges on one of the olefinic carbon atoms, the torsion angles between an aryl ring, and the adjacent unsaturated group as well as logP values. Three representative compounds were examined for their effect on respiration in rat liver mitochondria.

Entities:  

Mesh：

Substances：

Year:  2008        PMID： 18450457      PMCID： PMC3310918          DOI： 10.1016/j.bmc.2008.04.029

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  11 in total

1.  Cytotoxic analogues of 2,6-bis(arylidene)cyclohexanones.

Authors:  Jonathan R Dimmock; Maniyan P Padmanilayam; Gordon A Zello; Kurt H Nienaber; Theresa M Allen; Cheryl L Santos; Erik De Clercq; Jan Balzarini; Elias K Manavathu; James P Stables
Journal:  Eur J Med Chem       Date:  2003-02       Impact factor: 6.514

2.  Effect of inorganic phosphate concentration on the nature of inner mitochondrial membrane alterations mediated by Ca2+ ions. A proposed model for phosphate-stimulated lipid peroxidation.

Authors:  A J Kowaltowski; R F Castilho; M T Grijalba; E J Bechara; A E Vercesi
Journal:  J Biol Chem       Date:  1996-02-09       Impact factor: 5.157

3.  Degradation and inactivation of antitumor drugs.

Authors:  J A Benvenuto; T H Connor; D K Monteith; J L Laidlaw; S C Adams; T S Matney; J C Theiss
Journal:  J Pharm Sci       Date:  1993-10       Impact factor: 3.534

4.  3-(3,4,5-Trimethoxyphenyl)-1-oxo-2-propene: a novel pharmacophore displaying potent multidrug resistance reversal and selective cytotoxicity.

Authors:  Umashankar Das; Masami Kawase; Hiroshi Sakagami; Atsushi Ideo; Jun Shimada; Joseph Molnár; Zoltán Baráth; Zsuzsanna Bata; Jonathan R Dimmock
Journal:  Bioorg Med Chem       Date:  2007-03-13       Impact factor: 3.641

5.  3-Arylidene-1-(4-nitrophenylmethylene)-3,4-dihydro-1H-naphthalen-2-ones and related compounds displaying selective toxicity and reversal of multidrug resistance in neoplastic cells.

Authors:  Jonathan R Dimmock; Umashankar Das; H Inci Gul; Masami Kawase; Hiroshi Sakagami; Zoltán Baráth; Imre Ocsovsky; Joseph Molnár
Journal:  Bioorg Med Chem Lett       Date:  2005-03-15       Impact factor: 2.823

6.  Cytotoxic 5-aryl-1-(4-nitrophenyl)-3-oxo-1,4-pentadienes mounted on alicyclic scaffolds.

Authors:  Umashankar Das; H Inci Gul; Jane Alcorn; Anuraag Shrivastav; Theresa George; Rajendra K Sharma; Kurt H Nienaber; Erik De Clercq; Jan Balzarini; Masami Kawase; Noriyuki Kan; Toru Tanaka; Satoru Tani; Karl A Werbovetz; Adam J Yakovich; Elias K Manavathu; James P Stables; Jonathan R Dimmock
Journal:  Eur J Med Chem       Date:  2006-04-03       Impact factor: 6.514

7.  Design, synthesis, and biological evaluation of hybrid molecules containing alpha-methylene-gamma-butyrolactones and polypyrrole minor groove binders.

Authors:  Pier Giovanni Baraldi; Maria Del Carmen Nunez; Mojgan Aghazadeh Tabrizi; Erik De Clercq; Jan Balzarini; Jaime Bermejo; Francisco Estévez; Romeo Romagnoli
Journal:  J Med Chem       Date:  2004-05-20       Impact factor: 7.446

8.  Cytotoxic 1,3-diarylidene-2-tetralones and related compounds.

Authors:  Jonathan R Dimmock; Maniyan P Padmanilyam; Gordon A Zello; J Wilson Quail; Eliud O Oloo; Jared S Prisciak; Heinz Bernhard Kraatz; Arten Cherkasov; Jeremy S Lee; Theresa M Allen; Cheryl L Santos; Elias K Manavathu; Erik De Clercq; Jan Balzarini; James P Stables
Journal:  Eur J Med Chem       Date:  2002-10       Impact factor: 6.514

9.  Cytotoxic and topographical properties of 6-arylidene-2-dimethylaminomethylcyclohexanone hydrochlorides and related compounds.

Authors:  J R Dimmock; M Chamankhah; U Das; G A Zello; J W Quail; J Yang; K H Nienaber; R K Sharma; P Selvakumar; J Balzarini; E De Clercq; J P Stables
Journal:  J Enzyme Inhib Med Chem       Date:  2004-02       Impact factor: 5.051

10.  Effect of antineoplastic and cytotoxic Mannich Bases derived from conjugated styryl ketones on mitochondrial respiration in rat liver cells.

Authors:  N W Hamon; D L Bassendowski; D E Wright; J R Dimmock; L M Noble
Journal:  J Pharm Sci       Date:  1978-11       Impact factor: 3.534
View more
  7 in total

1.  Tumor-selective cytotoxicity of a novel pentadiene analogue on human leukemia/ lymphoma cells.

Authors:  Yahaira Santiago-Vázquez; Umashankar Das; Armando Varela-Ramirez; Sarah T Baca; Yoshira Ayala-Marin; Carolina Lema; Swagatika Das; Alaa Baryyan; Jonathan R Dimmock; Renato J Aguilera
Journal:  Clin Cancer Drugs       Date:  2016

2.  Cytotoxic 2-benzylidene-6-(nitrobenzylidene)cyclohexanones which display substantially greater toxicity for neoplasms than non-malignant cells.

Authors:  Umashankar Das; Alireza Doroudi; H Inci Gul; Hari N Pati; Masami Kawase; Hiroshi Sakagami; Qing Chu; James P Stables; Jonathan R Dimmock
Journal:  Bioorg Med Chem       Date:  2010-02-04       Impact factor: 3.641

3.  E-2-[3-(3,4-dichlorophenyl)-1-oxo-2-propenyl]-3-methylquinoxaline-1,4-dioxide: a lead antitubercular agent which alters mitochondrial respiration in rat liver.

Authors:  Umashankar Das; Swagatika Das; Brian Bandy; Dennis K J Gorecki; Jonathan R Dimmock
Journal:  Eur J Med Chem       Date:  2010-07-24       Impact factor: 6.514

Review 4.  1,5-diaryl-3-oxo-1,4-pentadienes: a case for antineoplastics with multiple targets.

Authors:  U Das; R K Sharma; J R Dimmock
Journal:  Curr Med Chem       Date:  2009       Impact factor: 4.530

5.  2-(3-Aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides: a novel cluster of tumor-specific cytotoxins which reverse multidrug resistance.

Authors:  Umashankar Das; Hari N Pati; Atulya K Panda; Erik De Clercq; Jan Balzarini; Joseph Molnár; Zoltán Baráth; Imre Ocsovszki; Masami Kawase; Li Zhou; Hiroshi Sakagami; Jonathan R Dimmock
Journal:  Bioorg Med Chem       Date:  2009-04-17       Impact factor: 3.641

6.  3,5-Bis(benzylidene)-4-oxo-1-phosphonopiperidines and related diethyl esters: Potent cytotoxins with multi-drug-resistance reverting properties.

Authors:  Swagatika Das; Umashankar Das; Ponniah Selvakumar; Rajendra K Sharma; Jan Balzarini; Erik De Clercq; Joseph Molnár; Julianna Serly; Zoltán Baráth; Gabriele Schatte; Brian Bandy; Dennis K J Gorecki; Jonathan R Dimmock
Journal:  ChemMedChem       Date:  2009-11       Impact factor: 3.466

7.  Novel Unsymmetric 3,5-Bis(benzylidene)-4-piperidones That Display Tumor-Selective Toxicity.

Authors:  Aruna Chhikara; Praveen K Roayapalley; Hiroshi Sakagami; Shigeru Amano; Keitaro Satoh; Yoshihiro Uesawa; Umashankar Das; Swagatika Das; Edgar A Borrego; Cristina D Guerena; Clare R Hernandez; Renato J Aguilera; Jonathan R Dimmock
Journal:  Molecules       Date:  2022-10-09       Impact factor: 4.927
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.