Tag: M.W=400-450

Nguyen, Anh Minh Thao published the artcileInfluence of N-methylation and conformation on almiramide anti-leishmanial activity, Product Details of C25H23NO4, the publication is Molecules (2021), 26(12), 3606, database is CAplus and MEDLINE.

The almiramide N-methylated lipopeptides exhibit promising activity against trypanosomatid parasites. A structure-activity relationship study has been performed to examine the influences of N-methylation and conformation on activity against various strains of leishmaniasis protozoan and on cytotoxicity. The synthesis and biol. anal. of twenty-five analogs demonstrated that derivatives with a single Me group on either the first or fifth residue amide nitrogen exhibited greater activity than the permethylated peptides and relatively high potency against resistant strains. Replacement of amino amide residues in the peptide, by turn inducing α amino γ lactam (Agl) and N-aminoimidazalone (Nai) counterparts, reduced typically anti-parasitic activity; however, peptide amides possessing Agl residues at the second residue retained significant potency in the unmethylated and permethylated series. Systematic study of the effects of methylation and turn geometry on anti-parasitic activity indicated the relevance of an extended conformer about the central residues, and conformational mobility by tertiary amide isomerization and turn geometry at the extremities of the active peptides.

Molecules published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Product Details of C25H23NO4.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Le Roux, Antoine published the artcileStructure-Permeability Relationship of Semipeptidic Macrocycles-Understanding and Optimizing Passive Permeability and Efflux Ratio, Recommanded Product: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is Journal of Medicinal Chemistry (2020), 63(13), 6774-6783, database is CAplus and MEDLINE.

We herein report the first thorough anal. of the structure-permeability relationship of semipeptidic macrocycles. In total, 47 macrocycles were synthesized using a hybrid solid-phase/solution strategy, and then their passive and cellular permeability was assessed using the parallel artificial membrane permeability assay (PAMPA) and Caco-2 assay, resp. The results indicate that semipeptidic macrocycles generally possess high passive permeability based on the PAMPA, yet their cellular permeability is governed by efflux, as reported in the Caco-2 assay. Structural variations led to tractable structure-permeability and structure-efflux relationships, wherein the linker length, stereoinversion, N-methylation, and peptoids site-specifically impact the permeability and efflux. Extensive NMR, mol. dynamics, and ensemble-based three-dimensional polar surface area (3D-PSA) studies showed that ensemble-based 3D-PSA is a good predictor of passive permeability.

Journal of Medicinal Chemistry published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Recommanded Product: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Mona, Christine E. published the artcileStructure-Activity Relationship and Signaling of New Chimeric CXCR4 Agonists, HPLC of Formula: 77128-73-5, the publication is Journal of Medicinal Chemistry (2016), 59(16), 7512-7524, database is CAplus and MEDLINE.

The CXCR4 receptor binds with meaningful affinities only CXCL12 and synthetic antagonists/inverse agonists. We recently described high affinity synthetic agonists for this chemokine receptor, obtained by grafting the CXCL12 N-terminus onto the inverse agonist T140. While those chimeric mols. behave as agonists for CXCR4, their binding and activation mode are unknown. The present SAR of those CXCL12-oligopeptide grafts reveals the key determinants involved in CXCR4 activation. Position 3 (Val) controls affinity, whereas position 7 (Tyr) acts as an efficacy switch. Chimeric mols. bearing aromatic residues in position 3 possess high binding affinities for CXCR4 and are Gα_i full agonists with robust chemotactic properties. Fine-tuning of electron-poor aromatic rings in position 7 enhances receptor activation. To rationalize these results, a homol. model of a receptor-ligand complex was built using the published crystal structures of CXCR4. Mol. dynamics simulations reveal further details accounting for the observed SAR for this series.

Journal of Medicinal Chemistry published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, HPLC of Formula: 77128-73-5.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Hilimire, Thomas A. published the artcileN-Methylation as a Strategy for Enhancing the Affinity and Selectivity of RNA-binding Peptides: Application to the HIV-1 Frameshift-Stimulating RNA, Application of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is ACS Chemical Biology (2016), 11(1), 88-94, database is CAplus and MEDLINE.

Human Immunodeficiency Virus (HIV) type 1 uses a -1 programmed ribosomal frameshift (-1 PRF) event to translate its enzymes from the same transcript used to encode the virus’ structural proteins. The frequency of this event is highly regulated, and significant deviation from the normal 5-10% frequency has been demonstrated to decrease viral infectivity. Frameshifting is primarily regulated by the Frameshift Stimulatory Signal RNA (FSS-RNA), a thermodynamically stable, highly conserved stem loop that has been proposed as a therapeutic target. We describe the design, synthesis, and testing of a series of N-Me peptides able to bind the HIV-1 FSS RNA stem loop with low nanomolar affinity and high selectivity. Surface plasmon resonance (SPR) data indicates increased affinity is a reflection of a substantially enhanced on rate. Compounds readily penetrate cell membranes and inhibit HIV infectivity in a pseudotyped virus assay. Viral infectivity inhibition correlates with compound-dependent changes in the ratios of Gag and Gag-Pol in virus particles. As the first compounds with both single digit nanomolar affinities for the FSS RNA and an ability to inhibit HIV in cells, these studies support the use of N-methylation for enhancing the affinity, selectivity, and bioactivity of RNA-binding peptides.

ACS Chemical Biology published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Application of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Fang, Wei-Jie published the artcileDeletion of Ac-NMePhe¹ from [NMePhe¹]arodyn under acidic conditions, part 2: effects of substitutions on pharmacological activity, Application of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is Biopolymers (2011), 96(1), 103-110, database is CAplus and MEDLINE.

Arodyn (Ac[Phe^1,2,3,Arg⁴,D-Ala⁸]Dyn A(1-11)NH₂) is an acetylated dynorphin A (Dyn A) analog that is a potent and selective κ opioid receptor antagonist, and its analog [NMePhe¹]arodyn shows even higher affinity and selectivity for κ opioid receptors. However, the latter compound is prone to deletion of the Ac-NMePhe moiety from the N-terminus of the peptide during acidic cleavage as described in the accompanying paper. Several stable analogs of [NMePhe¹]arodyn and [NMePhe¹,Trp³]arodyn where the acetyl group was substituted with a heteroatom-containing group were evaluated for their opioid receptor affinity, selectivity, and efficacy. Methoxycarbonyl derivatives exhibited the highest κ opioid receptor affinity among the analogs. Addnl. [CH₃OCO-NMePhe¹]arodyn analogs where position 3 was substituted with other aromatic or nonaromatic residues were also evaluated for κ receptor affinity, selectivity, and efficacy. [CH₃OCO-NMePhe¹]arodyn has similar κ opioid receptor affinity as [NMePhe¹]arodyn, retains high κ opioid receptor selectivity, and is a potent κ opioid receptor antagonist.

Biopolymers published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Application of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Barrulas, Pedro published the artcileSynthesis of novel cinchona-amino acid hybrid organocatalysts for asymmetric catalysis, Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is Tetrahedron: Asymmetry (2014), 25(12), 923-935, database is CAplus.

Three novel subclasses of cinchonidine derivatives coupled to diverse amino acids were prepared in very good overall yield and tested in a benchmark organocatalytic aldol reaction, between acetone and aromatic aldehydes. These subclasses are a family of amino acid-cinchonidine (subclass A), N-formamides-cinchonidine (subclass B) and dipeptide-cinchonidine (subclass C) hybrids. The main goal, besides obtaining very good yield and enantioselectivity was to understand the influence of the amino acid side chain residues on the enantioselectivity of the asym. aldol reactions. Different amino acid tethered cinchonidine hybrids were compared and their catalytic behavior was evaluated, allowing good enantioselectivity to be achieved, 92% ee in one case. Other reactions such as Biginelli, Michael addition and ketimine hydrosilylation reactions were screened with these ligands, but the outcome was less successful. The synthesis of the target compounds (organocatalysts) was achieved by a reaction of (8α,9S)-cinchonan-9-amine [epi-(amino)cinchonidine] with amino acids, such as N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]glycine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]–L-valine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]–L-tyrosine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alloisoleucine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-λ-methionine. The title compounds thus formed included chiral cinchona-alkaloid-amino acid derivatives, such as (2S)-2-amino-N-(8α,9S)-cinchonan-9-yl-3,3-(dimethyl)butanamide [i.e., N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-(methyl)-L-valine derivative], (2S)-N-[(8α,9S)-cinchonan-9-yl]-2-pyrrolidinecarboxamide (L-proline derivative).

Tetrahedron: Asymmetry published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Bann, Samantha J. published the artcileA chemical-intervention strategy to circumvent peptide hydrolysis by D-stereoselective peptidases, Recommanded Product: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is Journal of Medicinal Chemistry (2019), 62(22), 10466-10472, database is CAplus and MEDLINE.

D-Stereoselective peptidases that degrade nonribosomal peptides (NRPs) were recently discovered and could have serious implications for the future of NRPs as antibiotics. Herein, we report chem. modifications that can be used to impart resistance to the D-peptidases BogQ and TriF. New tridecaptin A analogs were synthesized that retain strong antimicrobial activity and have significantly enhanced D-peptidase stability. Invitro assays confirmed that synthetic analogs retain the ability to bind to their cellular receptor, peptidoglycan intermediate lipid II.

Journal of Medicinal Chemistry published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Recommanded Product: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Micewicz, Ewa D. published the artcileSmall lipidated anti-obesity compounds derived from neuromedin U, Application of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is European Journal of Medicinal Chemistry (2015), 616-626, database is CAplus and MEDLINE.

A small library of truncated/lipid-conjugated neuromedin U (NmU) analogs was synthesized and tested in vitro using an intracellular calcium signaling assay. The selected, most active analogs were then tested in vivo, and showed potent anorexigenic effects in a diet-induced obese (DIO) mouse model. The most promising compound, NM4-C₁₆ was effective in a once-weekly-dose regimen. Collectively, the authors’ findings suggest that short, lipidated analogs of NmU are suitable leads for the development of novel anti-obesity therapeutics.

European Journal of Medicinal Chemistry published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Application of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Kaminker, Revital published the artcileTuning of protease resistance in oligopeptides through N-alkylation, Product Details of C25H23NO4, the publication is Chemical Communications (Cambridge, United Kingdom) (2018), 54(69), 9631-9634, database is CAplus and MEDLINE.

N-Methylation of amino acids is an effective way to create protease resistance in both natural and synthetic peptides. However, alkyl substituents other than N-Me have not been extensively studied. Here, we prepare and examine a series of N-substituted peptides in which the size and length of the alkyl group is modulated. These design insights provide a unique and modular handle for tuning proteolysis in oligopeptides.

Chemical Communications (Cambridge, United Kingdom) published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Product Details of C25H23NO4.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem