2854-32-2 Usage
Description
BML-190 is a selective cannabinoid CB2 receptor agonist, which is a type of compound that can selectively bind to the CB2 receptor. This receptor is primarily found in the immune system and has been associated with various physiological processes. BML-190 has been studied for its potential therapeutic effects in different conditions.
Uses
Used in Pharmaceutical Industry:
BML-190 is used as a therapeutic agent for the treatment of organophosphate and carbamate toxicity. These are common toxic compounds that can cause severe health issues, and BML-190 has shown potential in mitigating their harmful effects.
Additionally, BML-190 is used as a therapeutic agent for the treatment of various conditions by targeting the CB2 receptor. Its agonistic activity on the CB2 receptor has been explored for its potential benefits in conditions such as inflammation, pain, and neurodegenerative diseases. The selective targeting of the CB2 receptor makes BML-190 a promising candidate for the development of novel treatments with fewer side effects compared to traditional medications.
Biological Activity
Potent and selective CB 2 receptor ligand (K i values are 435 nM and > 2 μ M for CB 2 and CB 1 respectively).
references
[1] new dc, wong yh. bml-190 and am251 act as inverse agonists at the human cannabinoid cb2 receptor: signalling via camp and inositol phosphates. febs lett. 2003 feb 11;536(1-3):157-60. pubmed pmid: 12586356.[2] chang yh, lee st, lin ww. effects of cannabinoids on lps-stimulated inflammatory mediator release from macrophages: involvement of eicosanoids. j cell biochem. 2001;81(4):715-23. pubmed pmid: 11329626.[3] klegeris a, bissonnette cj, mcgeer pl. reduction of human monocytic cell neurotoxicity and cytokine secretion by ligands of the cannabinoid-type cb2 receptor. br j pharmacol. 2003 jun;139(4):775-86. pubmed pmid: 12813001; pubmed central pmcid: pmc1573900. [4] scutt a, williamson em. cannabinoids stimulate fibroblastic colony formation by bone marrow cells indirectly via cb2 receptors. calcif tissue int. 2007 jan;80(1):50-9. epub 2007 jan 4. pubmed pmid: 17205329.[5] zhang l, zhang x, wu p, li h, jin s, zhou x, li y, ye d, chen b, wan j. bml-111, a lipoxin receptor agonist, modulates the immune response and reduces the severity of collagen-induced arthritis. inflamm res. 2008 apr;57(4):157-62. doi: 10. 1007/s00011-007-7141-z. pubmed pmid: 18648754.[6] zhang q, ma p, cole rb, wang g. in vitro metabolism of indomethacin morpholinylamide (bml-190), an inverse agonist for the peripheral cannabinoid receptor (cb(2)) in rat liver microsomes. eur j pharm sci. 2010 sep 11;41(1):163-72. doi: 10.1016/j.ejps.2010.06.004. epub 2010 jun 11. pubmed pmid: 20542112; pubmed central pmcid: pmc2907062.
Check Digit Verification of cas no
The CAS Registry Mumber 2854-32-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,8,5 and 4 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 2854-32:
(6*2)+(5*8)+(4*5)+(3*4)+(2*3)+(1*2)=92
92 % 10 = 2
So 2854-32-2 is a valid CAS Registry Number.
InChI:InChI=1/C23H23ClN2O4/c1-15-19(14-22(27)25-9-11-30-12-10-25)20-13-18(29-2)7-8-21(20)26(15)23(28)16-3-5-17(24)6-4-16/h3-8,13H,9-12,14H2,1-2H3
2854-32-2Relevant articles and documents
Water-removable ynamide coupling reagent for racemization-free syntheses of peptides, amides, and esters
Liu, Tao,Zhang, Xue,Peng, Zejun,Zhao, Junfeng
supporting information, p. 9916 - 9921 (2021/12/24)
A novel ynamide coupling reagent, the by-product of which can be removed by water, was reported. It promotes the direct coupling between carboxylic acids and amines, alcohols or thiols to provide amides, peptides, esters and thioesters, respectively. No detectable racemization was observed for all the coupling reactions of carboxylic acids containing an α-chiral center. Importantly, a simple acidic aqueous work-up removed the by-product readily to afford pure coupling products in good to excellent yields without the use of column chromatography, thus making this method more environmentally benign, user friendly and cost-effective. The robustness of the water-removable ynamide coupling reagent was further exemplified by the racemization/epimerization-free synthesis of carfilzomib, in which no column chromatography purification was involved for the entire 12-step synthesis.
Ester and amide derivatives of the nonsteroidal antiinflammatory drug, indomethacin, as selective cyclooxygenase-2 inhibitors
Kalgutkar, Amit S.,Marnett, Alan B.,Crews, Brenda C.,Remmel, Rory P.,Marnett, Lawrence J.
, p. 2860 - 2870 (2007/10/03)
Recent studies from our laboratory have shown that derivatization of the carboxylate moiety in substrate analogue inhibitors, such as 5,8,11,14- eicosatetraynoic acid, and in nonsteroidal antiinflammatory drugs (NSAIDs), such as indomethacin and meclofenamic acid, results in the generation of potent and selective cyclooxygenase-2 (COX-2) inhibitors (Kalgutkar et al. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 925-930). This paper summarizes details of the structure-activity studies involved in the transformation of the arylacetic acid NSAID, indomethacin, into a COX-2-selective inhibitor. Many of the structurally diverse indomethacin esters and amides inhibited purified human COX-2 with IC50 values in the low-nanomolar range but did not inhibit ovine COX-1 activity at concentrations as high as 66 μM. Primary and secondary amide analogues of indomethacin were more potent as COX-2 inhibitors than the corresponding tertiary amides. Replacement of the 4- chlorobenzoyl group in indomethacin esters or amides with the 4-bromobenzyl functionality or hydrogen afforded inactive compounds. Likewise, exchanging the 2-methyl group on the indole ring in the ester and amide series with a hydrogen also generated inactive compounds. Inhibition kinetics revealed that indomethacin amides behave as slow, tight-binding inhibitors of COX-2 and that selectivity is a function of the time-dependent step. Conversion of indomethacin into ester and amide derivatives provides a facile strategy for generating highly selective COX-2 inhibitors and eliminating the gastrointestinal side effects of the parent compound.