Literature DB >> 19320504

Synthesis and anticancer activity of new hydroxamic acid containing 1,4-benzodiazepines.

Lawrence P Tardibono1, Marvin J Miller.   

Abstract

By employing an intramolecular Pd(0)-mediated ring opening of an acylnitroso-derived cycloadduct, new hydroxamic acid containing benzodiazepines have been synthesized and have demonstrated biological activity in MCF-7 and PC-3 tumor cell lines. Subsequent N-O bond reduction of the hydroxamate has provided access to amide analogues for SAR studies. During the course of our syntheses, an intermediate oxazoline N-oxide was isolated and gave insight into the mechanism of the key Pd(0)-mediated reaction.

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Year:  2009        PMID： 19320504      PMCID： PMC2725444          DOI： 10.1021/ol900210h

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  12 in total

1.  Novel 1,4-benzodiazepines from acylnitroso-derived hetero-Diels-Alder cycloadducts.

Authors:  Matthew D Surman; Mark J Mulvihill; Marvin J Miller
Journal:  Org Lett       Date:  2002-01-10       Impact factor: 6.005

Review 2.  Inhibitors of farnesyltransferase: a rational approach to cancer chemotherapy?

Authors:  Ian M Bell
Journal:  J Med Chem       Date:  2004-04-08       Impact factor: 7.446

3.  Oxazoline N-oxide-mediated [2+3] cycloadditions. Application to a synthesis of (-)-tetrahydrolipstatin.

Authors:  O Dirat; C Kouklovsky; Y Langlois
Journal:  Org Lett       Date:  1999-09-09       Impact factor: 6.005

4.  Novel 1,4-benzodiazepine derivatives with antiproliferative properties on tumor cell lines.

Authors:  Jennifer Dourlat; Wang-Qing Liu; Nohad Gresh; Christiane Garbay
Journal:  Bioorg Med Chem Lett       Date:  2007-02-09       Impact factor: 2.823

5.  Chemoenzymatic asymmetric total synthesis of phosphodiesterase inhibitors: preparation of a polycyclic pyrazolo[3,4-d]pyrimidine from an acylnitroso Diels-Alder cycloadduct-derived aminocyclopentenol.

Authors:  May Xiao-Wu Jiang; Namal C Warshakoon; Marvin J Miller
Journal:  J Org Chem       Date:  2005-04-01       Impact factor: 4.354

6.  The immunomodulatory benzodiazepine Bz-423 inhibits B-cell proliferation by targeting c-myc protein for rapid and specific degradation.

Authors:  Thomas B Sundberg; Gina M Ney; Chitra Subramanian; Anthony W Opipari; Gary D Glick
Journal:  Cancer Res       Date:  2006-02-01       Impact factor: 12.701

7.  Protein farnesyltransferase inhibitors exhibit potent antimalarial activity.

Authors:  Laxman Nallan; Kevin D Bauer; Pravin Bendale; Kasey Rivas; Kohei Yokoyama; Carolyn P Hornéy; Prakash Rao Pendyala; David Floyd; Louis J Lombardo; David K Williams; Andrew Hamilton; Said Sebti; William T Windsor; Patricia C Weber; Frederick S Buckner; Debopam Chakrabarti; Michael H Gelb; Wesley C Van Voorhis
Journal:  J Med Chem       Date:  2005-06-02       Impact factor: 7.446

8.  Titanocene(III) chloride-mediated reductions of oxazines, hydroxamic acids, and N-hydroxy carbamates.

Authors:  Cara Cesario; Lawrence P Tardibono; Marvin J Miller
Journal:  J Org Chem       Date:  2009-01-02       Impact factor: 4.354

9.  Chemoenzymatic synthesis and synthetic application of enantiopure aminocyclopentenols: total synthesis of carbocyclic (+)-uracil polyoxin C and its alpha-epimer.

Authors:  Fangzheng Li; John B Brogan; Jennifer L Gage; Deyi Zhang; Marvin J Miller
Journal:  J Org Chem       Date:  2004-06-25       Impact factor: 4.354

10.  Crystal structures of the anticancer clinical candidates R115777 (Tipifarnib) and BMS-214662 complexed with protein farnesyltransferase suggest a mechanism of FTI selectivity.

Authors:  T Scott Reid; Lorena S Beese
Journal:  Biochemistry       Date:  2004-06-08       Impact factor: 3.162
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  9 in total

1.  A new approach to cyclic hydroxamic acids: Intramolecular cyclization of N-benzyloxy carbamates with carbon nucleophiles.

Authors:  Yuan Liu; Hollie K Jacobs; Aravamudan S Gopalan
Journal:  Tetrahedron       Date:  2011-03-25       Impact factor: 2.457

2.  Regio- and stereochemically controlled formation of hydroxamic acids from indium triflate-mediated nucleophilic ring-opening reactions with acylnitroso-Diels-Alder adducts.

Authors:  Baiyuan Yang; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2010-02-10       Impact factor: 2.415

3.  Syntheses of mycobactin analogs as potent and selective inhibitors of Mycobacterium tuberculosis.

Authors:  Raúl E Juárez-Hernández; Scott G Franzblau; Marvin J Miller
Journal:  Org Biomol Chem       Date:  2012-08-16       Impact factor: 3.876

4.  Indium triflate-assisted nucleophilic aromatic substitution reactions of nitrosobezene-derived cycloadducts with alcohols.

Authors:  Baiyuan Yang; Marvin J Miller
Journal:  Org Lett       Date:  2010-01-15       Impact factor: 6.005

5.  Regio- and stereoselective indium triflate-mediated nucleophilic ring-opening reactions of 3-aza-2-oxabicyclo[2.2.1]hept-5-ene and -[2.2.2]oct-5-ene systems.

Authors:  Baiyuan Yang; Marvin J Miller
Journal:  J Org Chem       Date:  2009-10-16       Impact factor: 4.354

6.  Identification of diverse modulators of central and peripheral circadian clocks by high-throughput chemical screening.

Authors:  Zheng Chen; Seung-Hee Yoo; Yong-Sung Park; Keon-Hee Kim; Shuguang Wei; Ethan Buhr; Zeng-You Ye; Hui-Lin Pan; Joseph S Takahashi
Journal:  Proc Natl Acad Sci U S A       Date:  2011-12-19       Impact factor: 11.205

7.  An Efficient Synthetic Approach Towards Benzo[b]pyrano[2,3-e][1,4]diazepines, and Their Cytotoxic Activity.

Authors:  Islam H El Azab; Nadia A A Elkanzi
Journal:  Molecules       Date:  2020-04-28       Impact factor: 4.411

8.  Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol.

Authors:  Beáta Fekete; Márta Palkó; Matti Haukka; Ferenc Fülöp
Journal:  Molecules       Date:  2017-04-13       Impact factor: 4.411

9.  Metal-free synthesis of 1,4-benzodiazepines and quinazolinones from hexafluoroisopropyl 2-aminobenzoates at room temperature.

Authors:  Jiewen Chen; En Liang; Jie Shi; Yinrong Wu; Kangmei Wen; Xingang Yao; Xiaodong Tang
Journal:  RSC Adv       Date:  2021-01-28       Impact factor: 3.361
  9 in total

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