195867-20-0

Usage

Chemical Properties

Beige powder

Upstream product

• 368870-66-0 ethyl (R)-4-((tert-butoxycarbonyl)amino)-5-phenylpentanoate 
• 790223-47-1 ethyl (R,E)-4-((tert-butoxycarbonyl)amino)-5-phenylpent-2-enoate 
• 139545-04-3 (E)-(S)-4-tert-Butoxycarbonylamino-5-phenyl-pent-2-enoic acid 
• 503606-59-5 (R)-4-(tert-butoxycarbonylamino)-5-phenylpentanoic acid methyl ester 
• 124818-94-6 ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate 
• 72155-45-4 Boc-L-phenylalaninal 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 63-91-2 L-phenylalanine 
• 109579-08-0 (S)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 197006-05-6 (R)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-ethyl]-carbamic acid tert-butyl ester 
• 237057-09-9 Boc-4-amino-3-hydroxy-5-phenylpentanoic acid ethyl ester 
• 99298-05-2 (E)-(S)-4-tert-butoxycarbonylamino-5-phenyl-pent-2-enoic acid methyl ester 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 139545-04-3 [L-(trans)]-4-[(t-butoxycarbonyl)amino]-5-phenyl-2-pentenoic acid 

Downstream Products

• 228864-44-6 (R)-Benzyl 5-phenyl-4-<(tert-butoxycarbonyl)amino>pentanoate 
• 1616684-82-2 tert-butyl (R)-5-(4-methylpiperazin-1-yl)-5-oxo-1-phenylpentan-2-ylcarbamate 
• 269078-74-2 (R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-phenylpentanoic acid 
• 63328-06-3 (4R)-4-amino-5-phenylpentanoic acid 
• 904324-80-7 {1-benzyl-4-[5-(3-methyl-1H-indazol-5-yl)-pyridin-3-yloxy]-butyl}-carbamic acid tert-butyl ester 
• 904324-65-8 [1-benzyl-4-(5-bromo-pyridin-3-yloxy)-butyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthetic method of chiral γ - amino acid and chiral γ - amino acid synthesized by adopting method (by machine translation)

The invention relates to a synthesis method of chiral γ - amino acid and chiral γ - amino acid synthesized by adopting the method, wherein an intermediate compound I is synthesized by amination reaction under the action of a catalyst under the action of a catalyst under the action of the catalyst. Ni / H2 Reduction in the system, re-Boc and Boc2 O react to form the intermediate compound II, and the ester group protecting group is removed under basic conditions, namely, chiral γ - amino acid is synthesized. Compared with the prior art, the method has the advantages that the process is simple, γ - amination reaction of unsaturated amide is catalyzed by cheap metal chiral cobalt complex to synthesize the intermediate compound I, chiral γ - amino acid with a substituent γ position can be synthesized directly and efficiently, and a novel method is provided for asymmetric catalytic synthesis of chiral γ - amino acids. (by machine translation)

Synthesis, antimycobacterial activity and influence on mycobacterial InhA and PknB of 12-membered cyclodepsipeptides

In recent years, several small natural cyclopeptides and cyclodepsipeptides were reported to have antimycobacterial activity. Following this lead, a synthetic pathway was developed for a small series of 12-membered ring compounds with one amide and two ester bonds (cyclotridepsipeptides). Within the series, the ring system proved to be necessary for growth inhibition of Mycobacterium smegmatis and Mycobacterium tuberculosis in the low micromolar range. Open-chain precursors and analogues were inactive. The compounds modulated autophosphorylation of the mycobacterial protein kinase B (PknB). PknB inhibitors were active at μM concentration against mycobacteria while inducers were inactive. PknB regulates the activity of the mycobacterial reductase InhA, the target of isoniazid. The activity of the series against Mycobacterium bovis BCG InhA overexpressing strains was indistinguishable from that of the parental strain suggesting that they do not inhibit InhA. All substances were not cytotoxic (HeLa > 5 μg/ml) and did not show any significant antiproliferative effect (HUVEC > 5 μg/ml; K-562 > 5 μg/ml). Within the scope of this study, the molecular target of this new type of small cyclodepsipeptide was not identified, but the data suggest interaction with PknB or other kinases may partly cause the activity.

Synthesis and biological activity of cyclolinopeptide A analogues modified with γ4-bis(homo-phenylalanine)

Cyclolinopeptide A (CLA), an immunosuppressive nonapeptide derived from linen seeds, was modified with S or R-γ4-bis(homo-phenylalanine) in positions 3 or 4, or both 3 and 4. These modifications changed the flexibility of new analogues and distribution of intramolecular hydrogen bonds. Analogues 11 c(Pro1-Pro2-Phe3-S-γ4-hhPhe4-Leu5-Ile6-Ile7-Leu8-Val9), 13 c(Pro1-Pro2-S-γ4-hhPhe3-R-γ4-hhPhe4-Leu5-Ile6-Ile7-Leu8-Val9) and 15 c(Pro1-Pro2-R-γ4-hhPhe3-Phe4-Leu5-Ile6-Ile7-Leu8-Val9) existed as a mixture of stable cis/trans isomers of Pro-Pro peptide bond. The comparison of the relative spatial orientations in crystal state of the two carbonyl groups, neighboring γ-amino acids, revealed conformational similarities to α-peptides. The addition of two -CH2- groups in γ-amino acids led to a more rigid conformation, although a more flexible one was expected. A significant difference in the relative orientation of the carbonyl groups was found for cyclic γ-peptides with a dominance of an antiparallel arrangement. As carbonyl groups may be engaged in the interactions with plausible receptors through hydrogen bonds, a similar biological activity of the modified peptides was expected. Our biological studies showed that certain cyclic, but not the corresponding linear peptides, lowered the viability of peripheral blood mononuclear cells (PBMC) at 100?μg/mL concentration. The proliferation of PBMC induced by phytohemagglutinin A (PHA) was strongly inhibited by cyclic peptides only, in a dose-dependant manner. On the other hand, lipopolysaccharide (LPS)-induced tumor necrosis factor alpha (TNF-α) production in whole blood cell cultures was inhibited by both linear and cyclic peptides. Peptide 15 c(Pro1-Pro2-R-γ4-hhPhe3-Phe4-Leu5-Ile6-Ile7-Leu8-Val9) blocked the expression of caspase-3, inhibited the expression of caspases-8 and -9 in 24?h culture of Jurkat cells, and caused DNA fragmentation in these cells, as an indicator of apoptosis. Thus, we revealed a new mechanism of immunosuppressive action of a nonapeptide.

Potent Antimicrobial Activity of Lipidated Short α,γ-Hybrid Peptides

Herein we report the potent antimicrobial activity of α,γ-hybrid lipopeptides composed of 1:1 alternating α- and γ-amino acids. Along with their potent antimicrobial activity against various Gram-positive and Gram-negative bacteria, these hybrid lipopepti

Antiplasmodial activity of new 4-aminoquinoline derivatives against chloroquine resistant strain

Emergence and spread of multidrug resistant strains of Plasmodium falciparum has severely limited the antimalarial chemotherapeutic options. In order to overcome the obstacle, a set of new side-chain modified 4-aminoquinolines were synthesized and screened against chloroquine-sensitive (3D7) and chloroquine-resistant (K1) strains of P. falciparum. The key feature of the designed molecules is the use of methylpiperazine linked α, β3- and γ-amino acids to generate novel side chain modified 4-aminoquinoline analogues. Among the evaluated compounds, 20c and 30 were found more potent than CQ against K1 and displayed a four-fold and a three-fold higher activity respectively, with a good selectivity index (SI = 5846 and 11,350). All synthesized compounds had resistance index between 1.06 and >14.13 as against 47.2 for chloroquine. Biophysical studies suggested that this series of compounds act on heme polymerization target.

Structure-activity relationships of 6-Methyl-benzo[ b ]thiophene-2- carboxylic Acid (1-{(S)-1-Benzyl-4-[4-(tetrahydropyran-4-ylmethyl)piperazin-1- yl]butylcarbamoyl}cyclopentyl)amide, potent antagonist of the neurokinin-2 receptor

As part of a project aimed at the identification of a series of small, orally available antagonists for the hNK2 receptor, starting from one of our capped dipeptide libraries, we succeeded in the chemical optimization of the first identified leads, finally producing a class of molecules with significant activity in our animal model after iv administration. We herein report the results of further chemical modifications made to reduce the overall peptide character of this series and the consequent improvement of their in vivo antagonist activity. The present work identified 6-methylbenzo[b]thiophene-2- carboxylic acid (1-{(S)-1-benzyl-4-[4-(tetrahydropyran-4-ylmethyl)piperazin-1- yl]butylcarbamoyl}cyclopentyl)amide (10i), endowed with subnanomolar potency in all the in vitro tests and being highly potent and of long duration upon in vivo testing after both iv and id dosing.

Tubulysin analogs incorporating desmethyl and dimethyl tubuphenylalanine derivatives

A series of tubulysin analogs in which one of the stereogenic centers of tubuphenylalanine was eliminated were synthesized. All compounds were tested for antiproliferative activity towards ovarian cancer cells and for inhibition of tubulin polymerization.

Trifluoroacetic acid-mediated intramolecular formal N-H insertion reactions with amino-α-diazoketones: A facile and efficient synthesis of optically pure pyrrolidinones and piperidinones

Trifluoroacetic acid (TFA) was found to promote intramolecular formal N-H insertion reactions. Upon treatment with TFA, optically pure N-Boc-β′-amino-α-diazoketones (5a-c) and N-Boc-γ′-amino-α-diazoketones (10a-d) can be converted, with retention of chira

Synthesis and evaluation of hapalosin and analogs as MDR-reversing agents

The marine natural product hapalosin and 22 analogs, which incorporated systematic substituent deletions or variations, were prepared. These compounds were evaluated in a cell-based assay for both MDR-reversing activity and general cytotoxicity. Some substituent modifications resulted in lower cytotoxicities, but most structural changes were either detrimental to or did not seriously alter the MDR-reversing activity.

Facile stereoselective synthesis of γ-substituted γ-amino acids from the corresponding α-amino acids

A facile stereoselective method for the synthesis of γ-substituted, γ-amino acids from α-amino acids was developed. The key step of the procedure is complete reduction of the keto functionality of α-amino acyl Meldrum's acid by sodium acetoxyborohydride. The resulting amino alkyl Meldrum's acid undergoes thermal decarboxylative ring closure to a 5-substituted pyrrolidinone which yields the corresponding γ-amino acid after basic hydrolysis. The overall yield of the procedure ranges from 40 to 65%.