Literature DB >> 21449610

3,5-Bis(benzylidene)-1-[3-(2-hydroxyethylthio)propanoyl]piperidin-4-ones: a novel cluster of potent tumor-selective cytotoxins.

Umashankar Das1, Hari N Pati, Hiroshi Sakagami, Ken Hashimoto, Masami Kawase, Jan Balzarini, Erik De Clercq, Jonathan R Dimmock.   

Abstract

Novel 3,5-bis(benzylidene)-1-[3-(2-hydroxyethylthio)propanoyl]piperidin-4-ones (3a-e) display potent cytotoxicity and a preferential lethality toward various neoplasms compared to some normal cells. The corresponding sulfonic acid analogues 5a-e and an isostere 4 demonstrated substantially lower activity. The leads 3d and 3e possess very high activity against colon cancer and leukemia cell lines, caused DNA fragmentation, and activated caspase-3 in HL-60 cells. The enones 3b-e were well tolerated in a short-term toxicity screen in mice.

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Year:  2011        PMID： 21449610      PMCID： PMC3346748          DOI： 10.1021/jm101595p

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  13 in total

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Authors:  C A Lipinski; F Lombardo; B W Dominy; P J Feeney
Journal:  Adv Drug Deliv Rev       Date:  2001-03-01       Impact factor: 15.470

2.  Chemosensitization by buthionine sulfoximine in vivo.

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3.  Interdependence between physical parameters and selection of substituent groups for correlation studies.

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Journal:  J Med Chem       Date:  1971-08       Impact factor: 7.446

4.  Molecular properties that influence the oral bioavailability of drug candidates.

Authors:  Daniel F Veber; Stephen R Johnson; Hung-Yuan Cheng; Brian R Smith; Keith W Ward; Kenneth D Kopple
Journal:  J Med Chem       Date:  2002-06-06       Impact factor: 7.446

5.  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

6.  A conformational and structure-activity relationship study of cytotoxic 3,5-bis(arylidene)-4-piperidones and related N-acryloyl analogues.

Authors:  J R Dimmock; M P Padmanilayam; R N Puthucode; A J Nazarali; N L Motaganahalli; G A Zello; J W Quail; E O Oloo; H B Kraatz; J S Prisciak; T M Allen; C L Santos; J Balzarini; E De Clercq; E K Manavathu
Journal:  J Med Chem       Date:  2001-02-15       Impact factor: 7.446

7.  N-Aroyl-3,5-bis(benzylidene)-4-piperidones: a novel class of antimycobacterial agents.

Authors:  Umashankar Das; Swagatika Das; Brian Bandy; James P Stables; Jonathan R Dimmock
Journal:  Bioorg Med Chem       Date:  2008-02-08       Impact factor: 3.641

8.  Role of cellular glutathione and glutathione S-transferase in the expression of alkylating agent cytotoxicity in human breast cancer cells.

Authors:  G Chen; D J Waxman
Journal:  Biochem Pharmacol       Date:  1994-03-15       Impact factor: 5.858

Review 9.  The National Cancer Institute: cancer drug discovery and development program.

Authors:  M R Grever; S A Schepartz; B A Chabner
Journal:  Semin Oncol       Date:  1992-12       Impact factor: 4.929

10.  Toxicities derived from anti-tumor screening data.

Authors:  F R Quinn; G W Milne
Journal:  Fundam Appl Toxicol       Date:  1986-02
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  5 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.  Novel 3,5-bis(arylidene)-4-oxo-1-piperidinyl dimers: structure-activity relationships and potent antileukemic and antilymphoma cytotoxicity.

Authors:  Yahaira Santiago-Vazquez; Swagatika Das; Umashankar Das; Elisa Robles-Escajeda; Nora M Ortega; Carolina Lema; Armando Varela-Ramírez; Renato J Aguilera; Jan Balzarini; Erik De Clercq; Stephen G Dimmock; Dennis K J Gorecki; Jonathan R Dimmock
Journal:  Eur J Med Chem       Date:  2014-03-06       Impact factor: 6.514

3.  A novel class of piperidones exhibit potent, selective and pro-apoptotic anti-leukemia properties.

Authors:  Larissa M Nunes; Mohammad Hossain; Armando Varela-Ramirez; Umashankar DAS; Yoshira M Ayala-Marin; Jonathan R Dimmock; Renato J Aguilera
Journal:  Oncol Lett       Date:  2016-04-20       Impact factor: 2.967

4.  Multicomponent Domino Synthesis, Anticancer Activity and Molecular Modeling Simulation of Complex Dispirooxindolopyrrolidines.

Authors:  Natarajan Arumugam; Abdulrahman I Almansour; Raju Suresh Kumar; Periyasami Govindasami; Dhaifallah M Al-Thamili; Rajapandian Krishnamoorthy; Vaiyapuri Subbarayan Periasamy; Ali A Alshatwi; S M Mahalingam; Shankar Thangamani; J Carlos Menéndez
Journal:  Molecules       Date:  2018-05-05       Impact factor: 4.411

5.  A One-Pot Three-Component Synthesis and Investigation of the In Vitro Mechanistic Anticancer Activity of Highly Functionalized Spirooxindole-Pyrrolidine Heterocyclic Hybrids.

Authors:  Raju Suresh Kumar; Dhaifallah M Al-Thamili; Abdulrahman I Almansour; Natarajan Arumugam; Faruq Mohammad
Journal:  Molecules       Date:  2020-11-27       Impact factor: 4.411
  5 in total

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