Literature DB >> 20589293

Nitrogen-bound diazeniumdiolated amidines.

Debanjan Biswas1, Jeffrey R Deschamps, Larry K Keefer, Joseph A Hrabie.   

Abstract

In contrast to amidines bearing ionizable alpha-CH bonds, which react with nitric oxide (NO) to add diazeniumdiolate groups at their alpha-carbons, benzamidine forms an N-bound diazeniumdiolate that can be further derivatized at the other amidine nitrogen and/or the terminal oxygen to form caged NO compounds as potential NO prodrugs.

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Year:  2010        PMID： 20589293      PMCID： PMC6959519          DOI： 10.1039/c0cc00849d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  13 in total

1.  The secondary amine/nitric oxide complex ion R(2)N[N(O)NO](-) as nucleophile and leaving group in S9N)Ar reactions.

Authors:  J E Saavedra; A Srinivasan; C L Bonifant; J Chu; A P Shanklin; J L Flippen-Anderson; W G Rice; J A Turpin; K M Davies; L K Keefer
Journal:  J Org Chem       Date:  2001-05-04       Impact factor: 4.354

2.  Synthesis and in vitro anti-leukemic activity of structural analogues of JS-K, an anti-cancer lead compound.

Authors:  Harinath Chakrapani; Michael M Goodblatt; Vidya Udupi; Swati Malaviya; Paul J Shami; Larry K Keefer; Joseph E Saavedra
Journal:  Bioorg Med Chem Lett       Date:  2008-01-04       Impact factor: 2.823

3.  Conversion of proteins to diazeniumdiolate-based nitric oxide donors.

Authors:  J A Hrabie; J E Saavedra; P P Roller; G J Southan; L K Keefer
Journal:  Bioconjug Chem       Date:  1999 Sep-Oct       Impact factor: 4.774

4.  Diazeniumdiolate ions as leaving groups in anomeric displacement reactions: a protection-deprotection strategy for ionic diazeniumdiolates.

Authors:  Brett M Showalter; Melissa M Reynolds; Carlos A Valdez; Joseph E Saavedra; Keith M Davies; John R Klose; Gwendolyn N Chmurny; Michael L Citro; Joseph J Barchi; Scott I Merz; Mark E Meyerhoff; Larry K Keefer
Journal:  J Am Chem Soc       Date:  2005-10-19       Impact factor: 15.419

5.  Reaction of nitric oxide at the beta-carbon of enamines. A new method of preparing compounds containing the diazeniumdiolate functional group.

Authors:  J A Hrabie; E V Arnold; M L Citro; C George; L K Keefer
Journal:  J Org Chem       Date:  2000-09-08       Impact factor: 4.354

6.  Glycosylated PROLI/NO derivatives as nitric oxide prodrugs.

Authors:  Rahul S Nandurdikar; Anna E Maciag; Sam Y Hong; Harinath Chakrapani; Michael L Citro; Larry K Keefer; Joseph E Saavedra
Journal:  Org Lett       Date:  2010-01-01       Impact factor: 6.005

Review 7.  The nitric oxide prodrug JS-K and its structural analogues as cancer therapeutic agents.

Authors:  Anna E Maciag; Joseph E Saavedra; Harinath Chakrapani
Journal:  Anticancer Agents Med Chem       Date:  2009-09-01       Impact factor: 2.505

8.  Synthesis, mechanistic studies, and anti-proliferative activity of glutathione/glutathione S-transferase-activated nitric oxide prodrugs.

Authors:  Harinath Chakrapani; Ravi C Kalathur; Anna E Maciag; Michael L Citro; Xinhua Ji; Larry K Keefer; Joseph E Saavedra
Journal:  Bioorg Med Chem       Date:  2008-09-30       Impact factor: 3.641

9.  Synthesis and evaluation of piperazine and homopiperazine analogues of JS-K, an anti-cancer lead compound.

Authors:  Rahul S Nandurdikar; Anna E Maciag; Michael L Citro; Paul J Shami; Larry K Keefer; Joseph E Saavedra; Harinath Chakrapani
Journal:  Bioorg Med Chem Lett       Date:  2009-03-28       Impact factor: 2.823

10.  Hydrolytic reactivity trends among potential prodrugs of the O2-glycosylated diazeniumdiolate family. Targeting nitric oxide to macrophages for antileishmanial activity.

Authors:  Carlos A Valdez; Joseph E Saavedra; Brett M Showalter; Keith M Davies; Thomas C Wilde; Michael L Citro; Joseph J Barchi; Jeffrey R Deschamps; Damon Parrish; Stefan El-Gayar; Ulrike Schleicher; Christian Bogdan; Larry K Keefer
Journal:  J Med Chem       Date:  2008-06-06       Impact factor: 7.446
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  2 in total

1.  O2-functionalized methylamine diazeniumdiolates: evidence for E ⇄ Z equilibration in an acyclic system.

Authors:  Debanjan Biswas; Ryan J Holland; Jeffrey R Deschamps; Zhao Cao; Larry K Keefer; Joseph E Saavedra
Journal:  J Org Chem       Date:  2012-11-20       Impact factor: 4.354

2.  Aminolysis of an N-diazeniumdiolated amidine as an approach to diazeniumdiolated ammonia.

Authors:  Debanjan Biswas; Joseph A Hrabie; Joseph E Saavedra; Zhao Cao; Larry K Keefer; Joseph Ivanic; Ryan J Holland
Journal:  J Org Chem       Date:  2014-05-05       Impact factor: 4.354
  2 in total

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