PMID- 18220331
OWN - NLM
STAT- MEDLINE
DCOM- 20080519
LR  - 20131121
IS  - 0022-2623 (Print)
IS  - 0022-2623 (Linking)
VI  - 51
IP  - 4
DP  - 2008 Feb 28
TI  - N(G)-aminoguanidines from primary amines and the preparation of nitric oxide 
      synthase inhibitors.
PG  - 924-31
LID - 10.1021/jm701119v [doi]
AB  - A concise, general, and high-yielding method for the preparation of 
      N(G)-aminoguanidines from primary amines is reported. Using available and readily 
      prepared materials, primary amines are converted to protected 
      N(G)-aminoguanidines in a one-pot procedure. The method has been successfully 
      applied to a number of examples including the syntheses of four nitric oxide 
      synthase (NOS) inhibitors. The inhibitors prepared were investigated as 
      competitive inhibitors and as mechanistic inactivators of the inducible isoform 
      of NOS (iNOS). In addition, one of the four inhibitors prepared, 
      N(G)-amino-N(G)-2,2,2-trifluoroethyl-L-arginine 19, displays the unique ability 
      to both inhibit NO formation and prevent NADPH consumption by iNOS without 
      irreversible inactivation of the enzyme.
FAU - Martin, Nathaniel I
AU  - Martin NI
AD  - Department of Chemistry,Division of Physical Sciences, Lawrence Berkeley National 
      Laboratory, University of California, Berkeley 94720-3220, USA.
FAU - Beeson, William T
AU  - Beeson WT
FAU - Woodward, Joshua J
AU  - Woodward JJ
FAU - Marletta, Michael A
AU  - Marletta MA
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20080126
PL  - United States
TA  - J Med Chem
JT  - Journal of medicinal chemistry
JID - 9716531
RN  - 0 (Amines)
RN  - 0 (Guanidines)
RN  - 0 (N(G)-amino-N(G)-2,2,2-trifluoroethylarginine)
RN  - 31C4KY9ESH (Nitric Oxide)
RN  - 53-59-8 (NADP)
RN  - 94ZLA3W45F (Arginine)
RN  - EC 1.14.13.39 (Nitric Oxide Synthase)
RN  - EC 1.14.13.39 (Nitric Oxide Synthase Type II)
SB  - IM
MH  - Amines/*chemistry
MH  - Arginine/*analogs & derivatives/chemical synthesis/chemistry/pharmacology
MH  - Guanidines/*chemical synthesis/chemistry
MH  - NADP/chemistry
MH  - Nitric Oxide/chemical synthesis
MH  - Nitric Oxide Synthase/*antagonists & inhibitors/chemistry
MH  - Nitric Oxide Synthase Type II/antagonists & inhibitors/chemistry
MH  - Oxidation-Reduction
MH  - Stereoisomerism
MH  - Structure-Activity Relationship
EDAT- 2008/01/29 09:00
MHDA- 2008/05/20 09:00
CRDT- 2008/01/29 09:00
PHST- 2008/01/29 09:00 [pubmed]
PHST- 2008/05/20 09:00 [medline]
PHST- 2008/01/29 09:00 [entrez]
AID - 10.1021/jm701119v [doi]
PST - ppublish
SO  - J Med Chem. 2008 Feb 28;51(4):924-31. doi: 10.1021/jm701119v. Epub 2008 Jan 26.