A Convenient Reagent for N-hydroxyguanylation

Jirgensons, Aigars; Kums, I.; Kauss, Valerjans; Kalviņš, Ivars

doi:10.1080/00397919708005034

Cited by 10 publications

(8 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It could also be used in the synthesis of N, N'-disubstituted-N''-hydroxyguanidines although these compounds are not NOS substrates. A convenient reagent, 1-benzyloxy-3-benzyloxycarbonylthiourea, was developed for N-hydroxyguanylation [15]. When treated with an amine, it will give N-and O-protected hydroxyguanidine derivatives.…”

Section: Ii2 Synthesis Of N-hydroxyguanidinesmentioning

confidence: 99%

N-Hydroxyguanidines as Substrates of Nitric Oxide Synthases

Cai¹,

Lu²,

Wang³

2005

CTMC

View full text Add to dashboard Cite

Nitric oxide (NO) has been implicated in a wide variety of disease states. Both inhibitors and substrates of nitric oxide synthase (NOS) could have great therapeutic potential in the treatment of these diseases. There is considerable pharmacological interest in developing inhibitors of NOS, and hundreds of inhibitors have been identified. In contrast, the study on NOS substrates is less active. The advances in the identification, design and development of NOS substrates are discussed in this review. The focus is the chemistry and biochemistry of N-hydroxyguanidines. The crystal structures of substrates bound to NOSs and the mechanisms of NOS catalyzed NO generation from substrates are also discussed.

show abstract

Section: Ii2 Synthesis Of N-hydroxyguanidinesmentioning

confidence: 99%

N-Hydroxyguanidines as Substrates of Nitric Oxide Synthases

Cai¹,

Lu²,

Wang³

2005

CTMC

View full text Add to dashboard Cite

show abstract

“…This procedure is general for other carbamoyl isothiocyanates (ethyl carbamate, benzyl carbamate (Cbz), 2,2,2-trichloro-1,1-dimethylethyl carbamate, fluorenylmethyl carbamate (Fmoc), and phenyl carbamate) which allows synthetic flexibility in the deprotection. 18 (Scheme 7, Table 7). The Cbz strategy was chosen because cleavage of the Cbz and benzyl groups could be accomplished simultaneously.…”

mentioning

confidence: 99%

Recent developments in guanylating agents

Katritzky¹,

Rogovoy²

2005

Arkivoc

143

View full text Add to dashboard Cite

Dedicated to Professor Nikolai Zefirov on the occasion of his 70th birthday (received 26 Oct 04; accepted 08 Jan 05; published on the web 05 Jan 05) AbstractGuanidines are important molecules with a wide range of interesting properties. In this overview we summarize recent advances in the development of guanylating reagents which we define as compounds forming a guanidine structure by a chemical transformation. We cover important classes of guanylating agents developed in the last two decades and representative examples are reported.

show abstract

“…These observations suggest that O-protected N G -hydroxythioureas are prone to a competitive exchange of the hydroxylamine moiety in the presence of another amine to yield a more stable thiourea. This may also explain the modest yields (34−67%) reported by Jirgensons and co-workers in their preparation of protected N G -hydroxguanidines 3 …”

mentioning

confidence: 97%

“…As a first attempt, the protected 4,4-difluoro- N G -hydroxy- l -arginine species ( 5 ) was prepared in modest yield starting from Kim's precursor difluoroamine 3 7 and employing the thiourea reagent ( 4 ) based method of Jirgensons and co-workers . Disappointingly, the final deprotection step (under a variety of conditions) following this route led to complete loss of the N G -hydroxyguanidine functionality by overreduction (Scheme )…”

mentioning

confidence: 99%

“…We reasoned that by using an acid-labile protecting group for the N -hydroxy moiety it might still be possible to make use of a thiourea-based reagent approach. To this end, the N -Cbz/OTHP protected N G -hydroxythiourea 9 was prepared by reaction of Cbz-NCS ( 7 ) (formed in situ) and O-THP-protected hydroxylamine 13 ( 8 ) following the procedure of Jirgensons and co-workers (Scheme ) 2 …”

mentioning

confidence: 99%

See 1 more Smart Citation

N^G-Hydroxyguanidines from Primary Amines

2006

View full text Add to dashboard Cite

A concise and general method for the preparation of N(G)-hydroxyguanidines from primary amines is reported. Using available and readily prepared materials, primary amines are converted to protected N(G)-hydroxyguanidines in a one-pot procedure followed by deprotection under nonreducing conditions. The method has been successfully applied to a number of examples including a high-yielding preparation of N(G)-hydroxy-L-arginine, the intermediate in the enzymatic conversion of L-arginine to nitric oxide and L-citrulline by nitric oxide synthase.

show abstract

A Convenient Reagent for N-hydroxyguanylation

Cited by 10 publications

References 7 publications

N-Hydroxyguanidines as Substrates of Nitric Oxide Synthases

N-Hydroxyguanidines as Substrates of Nitric Oxide Synthases

Recent developments in guanylating agents

N^G-Hydroxyguanidines from Primary Amines

Contact Info

Product

Resources

About

A Convenient Reagent for N-hydroxyguanylation

Cited by 10 publications

References 7 publications

N-Hydroxyguanidines as Substrates of Nitric Oxide Synthases

N-Hydroxyguanidines as Substrates of Nitric Oxide Synthases

Recent developments in guanylating agents

NG-Hydroxyguanidines from Primary Amines

Contact Info

Product

Resources

About

N^G-Hydroxyguanidines from Primary Amines