cas 10065-79-9, Nsc293361 | Articles data

Articles about 10065-79-9Total 12 be found

Total Synthesis of Teixobactin
The first total synthesis of the cyclic depsipeptide natural product teixobactin is described. Synthesis was achieved by solid-phase peptide synthesis, incorporating the unusual l-allo-enduracididine as a suitably protected synthetic cassette and employing a key on-resin esterification and solution-phase macrolactamization. The synthetic natural product was shown to possess potent antibacterial activity against a range of Gram-positive pathogenic bacteria, including a virulent strain of Mycobacterium tuberculosis and methicillin-resistant Staphylococcus aureus (MRSA).
Giltrap, Andrew M.,Dowman, Luke J.,Nagalingam, Gayathri,Ochoa, Jessica L.,Linington, Roger G.,Britton, Warwick J.,Payne, Richard J.
p. 2788 - 2791
(2016)
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Orthoamides by selective borohydride reduction of N,N′,N″-triacyl- and N,N′,N″-tri(alkoxycarbonyl)-guanidines
N,N′,N″-Triacylguanidines and N,N′,N″-tri(alkoxycarbonyl)guanidines were prepared and reduced with borohydride salts in a mixture of tetrahydrofuran and acetic acid to give triacyl and tri(alkoxycarbonyl) orthoamides in yields of 40–85%. However, similar
Davis, Matthew C.,Groshens, Thomas J.
supporting information
p. 427 - 431
(2019/01/05)

Synthesis, SAR and selectivity of 2-acyl- and 2-cyano-1-hetarylalkyl- guanidines at the four histamine receptor subtypes: A bioisosteric approach
In the search for potential bioisosteres of the 4-imidazolyl ring in acylguanidines (e.g. UR-AK24), known to possess affinity to several histamine receptor subtypes (HxR, x = 1-4), and cyanoguanidine-type H 4R agonists (e.g. UR-PI376
Geyer, Roland,Igel, Patrick,Kaske, Melanie,Elz, Sigurd,Buschauer, Armin
supporting information
p. 72 - 81
(2014/01/06)

Process for the preparation of substituted pyrimidine derivatives
The present invention is directed to processes for the preparation of substituted pyrimidine derivatives, useful as intermediates in the synthesis of histamine H4 receptor modulators, and to intermediates in H4 modulator synthesis.
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Page/Page column 18

(2010/02/16)

Ng-acylated imidazolylpropylguanidines as potent histamine H4 receptor agonists: selectivity by variation of the n g-substituent?
3-(1H-Imidazol-4-yl)propylguanidine (SK&F 91486, 4) was identified as a potent partial agonist at the human histamine H3 receptor (hH3R) and human histamine H4 receptor (hH4R). With the aim to increase selectivity for the
Igel, Patrick,Schneider, Erich,Schnell, David,Elz, Sigurd,Seifert, Roland,Buschauer, Armin
supporting information; experimental part
p. 2623 - 2627
(2010/03/24)

Enantioselective syntheses of α-Fmoc-Pbf-[2-13C]-L- arginine and Fmoc-[1,3-13C2]-L-proline and incorporation into the neurotensin receptor 1 ligand, NT8-13
(Chemical Equation Presented) Enantioselective syntheses of selectively labeled, orthogonally protected [2-13C]-L-arginine and [1,3- 13C2]-L-proline are described from the commercially available precursors [2-13C]bromoacetic acid and potassium [ 13C]cyanide. Interestingly the enhanced signal assigned to C-2 in the 13C NMR spectrum of α-Fmoc-Pbf-[2-13C]-L-arginine was very broad at room temperature. The two Fmoc-labeled amino acids were used to prepare [2-13C]-Arg9 and [1,3-13C2]-Pro10 labeled ligand (NT8-13) by manual Fmoc-SPSS.
Song, Chuanjun,Tapaneeyakorn, Satita,Murphy, Annabel C.,Butts, Craig,Watts, Anthony,Willis, Christine L.
scheme or table
p. 8980 - 8987
(2010/03/02)

High yielding selective access to spirocyclopropanated 5-oxopiperazine-2- carboxylates and 1,4-diazepane-2,5-diones from methyl 2-chloro-2- cyclopropylideneacetate
The 2-spirocyclopropanated methyl 5-oxopiperazine-2-carboxylate 3 and the 3-spirocyclopropanated 6-chloro-1,4-diazepane-2,5-dione 4 could both be prepared at choice in 93 and 88% yield, respectively, from methyl 2-chloro-2- cyclopropylideneacetate (1) in a sequence of Michael addition of 3-benzyloxypropylamine, peptide coupling with N-Boc-glycine, Boc-group removal and cyclization. Transformation of the benzyloxypropyl side chain, peptide coupling with N-Boc-(S)-asparagine, deprotection and repeated cyclization led to the octahydro[2H]pyrazino[1,2-a]pyrazinetrione scaffold 10 containing a rigidified mimic of a tripeptide with a DGR motif. The overall yield of 11 after deprotection of 10 (a total of 13 steps in 8 distinct operations) was 30%. The Royal Society of Chemistry 2008.
Limbach, Michael,Korotkov, Vadim S.,Es-Sayed, Mazen,De Meijere, Armin
experimental part
p. 3816 - 3822
(2009/02/05)

Acylguanidines as bioisosteres of guanidines: NG-acylated imidazolylpropylguanidines, a new class of histamine h2 receptor agonists
N1-Aryl(heteroaryl)alkyl-N2-[3-(1H-imidazol-4-yl) propyl]guanidines are potent histamine H2-receptor (H2R) agonists, but their applicability is compromised by the lack of oral bioavailability and CNS penetration. To improve pharmacokinetics, we introduced carbonyl instead of methylene adjacent to the guanidine moiety, decreasing the basicity of the novel H2R agonists by 4-5 orders of magnitude. Some acylguanidines with one phenyl ring were even more potent than their diaryl analogues. As demonstrated by HPLC-MS, the acylguanidines (bioisosteres of the alkylguanidines) were absorbed from the gut of mice and detected in brain. In GTPase assays using recombinant receptors, acylguanidines were more potent at the guinea pig than at the human H2R. At the hH1R and hH3R, the compounds were weak to moderate antagonists or partial agonists. Moreover, potent partial hH4R agonists were identified. Receptor subtype selectivity depends on the imidazolylpropylguanidine moiety (privileged structure), opening an avenue to distinct pharmacological tools including potent H4R agonists.
Ghorai, Prasanta,Kraus, Anja,Keller, Max,G?tte, Carsten,Igel, Patrick,Schneider, Erich,Schnell, David,Bernhardt, Günther,Dove, Stefan,Zabel, Manfred,Elz, Sigurd,Seifert, Roland,Buschauer, Armin
scheme or table
p. 7193 - 7204
(2009/10/02)

Beta lactam compounds and their use as inhibitors of tryptase
Compounds of the formulas: are disclosed. These compounds inhibit tryptase as well as other enzyme systems or are selective tryptase inhibitors and are useful as antiinflammatory agents particularly in the treatment of chronic asthma.
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(2010/11/29)

Triurethane-protected guanidines and triflyldiurethane-protected guanidines: New reagents for guanidinylation reactions
New guanidinylation reagents are reported. These reagents consist of N,N',N''-tri-Boc-guanidine (1) and N,N',N''-tri-Cbz-guanidine (2), which allow for the facile conversion of alcohols to substituted guanidines. A series of arginine analogues were synthesized via condensation of a primary or secondary alcohol with the guanidinylation reagents 1 or 2, under Mitsunobu conditions, to produce protected alkylated guanidines. In addition, an extended study of the previously reported reagents N,N'-di-Boc-N''- triflylguanidine (3) and N,N'-di-Cbz-N''-triflylguanidine (4) is presented. The triflyldiurethane-protected guanidine 3 was utilized to guanidinylate primary and secondary amines under mild conditions with high yield in both solution and on solid phase.
Feichtinger, Konrad,Sings, Heather L.,Baker, Tracy J.,Matthews, Kenneth,Goodman, Murray
p. 8432 - 8439
(2007/10/03)

Conversion of alcohols to protected guanidines using the Mitsunobu protocol
An efficient method for the direct conversion of alcohols to guanidines is presented. A variety of alcohols react with 1 and 2 under Mitsunobu conditions to give the corresponding guanidines in high yield.
Dodd, Dharmpal S.,Kozikowski, Alan P.
p. 977 - 980
(2007/10/02)