133565-49-8 Usage
Description
BOC-L-THIOCITRULLINE-OTBU, also known as Boc-L-thiocitrulline tert-Butyl Ester, is a chemical compound and an analogue of L-thiocitrulline. It is characterized by its ability to act as an inhibitor of the isoforms of nitric oxide synthase (NOS), which plays a crucial role in various biological processes and diseases.
Uses
Used in Pharmaceutical Industry:
BOC-L-THIOCITRULLINE-OTBU is used as a research compound for the development of novel therapeutic agents targeting nitric oxide synthase (NOS) isoforms. Its application in this industry is due to its potential to modulate the activity of NOS, which is implicated in various pathological conditions, including inflammation, pain, and neurodegenerative diseases.
Used in Research and Development:
BOC-L-THIOCITRULLINE-OTBU serves as a valuable tool in the field of research and development, particularly in the study of nitric oxide synthase (NOS) and its role in cellular processes. It is used to investigate the mechanisms of NOS inhibition and to identify potential therapeutic targets for the treatment of diseases associated with NOS dysregulation.
Used in Drug Design and Synthesis:
In the field of drug design and synthesis, BOC-L-THIOCITRULLINE-OTBU is employed as a starting material or a structural component in the development of new drugs that target nitric oxide synthase (NOS). Its unique chemical properties and inhibitory activity make it a promising candidate for the design of novel pharmaceuticals with improved efficacy and selectivity.
Check Digit Verification of cas no
The CAS Registry Mumber 133565-49-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,3,5,6 and 5 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 133565-49:
(8*1)+(7*3)+(6*3)+(5*5)+(4*6)+(3*5)+(2*4)+(1*9)=128
128 % 10 = 8
So 133565-49-8 is a valid CAS Registry Number.
133565-49-8Relevant articles and documents
Heterocyclic analogues of L-citrulline as inhibitors of the isoforms of nitric oxide synthase (NOS) and identification of N(δ)-(4,5-dihydrothiazol-2-yl)ornithine as a potent inhibitor
Ulhaq, Saraj,Chinje, Edwin C.,Naylor, Matthew A.,Jaffar, Mohammed,Stratford, Ian J.,Threadgill, Michael D.
, p. 1787 - 1796 (2007/10/03)
L-Thiocitrulline is a known potent inhibitor of several isoforms of nitric oxide synthase (NOS). To explore the structure-activity relationships (SARs) for this molecule in more depth than has previously been reported, three analogues substituted at the sulphur of the isothioureas have been synthesised. In two of these, the S-substituent was 'tied back' sterically by cyclisation to the nitrogen remote from the amino-acid unit. N(δ)-(4,5-Dihydrothiazol-2-yl)ornithine was identified as an inhibitor of rat inducible and constitutive isoforms of NOS and of a constitutive NOS derived from a human tumour xenograft. Analogous N(δ)-(thiazol-2-yl)ornithines were less active, whereas the corresponding N(δ)-(oxazol-2-yl)ornithine and N(δ)-(pyrimidin-2-yl)ornithine failed completely to inhibit NOS. A new efficient preparation of the critical synthetic intermediate, N(α)-Boc-thiocitrulline t-butyl ester, has been developed. Further exploration of the SAR with 2-amino-5-(heterocyclylthio)pentanoic acids (synthesised from 2-(Boc-amino)-5-bromopentanoic acid t-butyl ester), with N-(4-aminobutyl)thiourea and with 2-(4-aminobutylamino)-4,5-dihydrothiazole enabled refinement of our previous model for binding of the substrate, L-arginine, and the inhibitors to NOS.
Synthesis of the putative L-arginine metabolite L-N(G)-hydroxyarginine
Feldman
, p. 875 - 878 (2007/10/02)
Syntheses of L-N(G)-hydroxyarginine (1), the putative biosynthetic precursor of nitric oxide, and the 15N labelled analogs 9 and 10 using L-ornithine as the enantiopure starting material is reported.
