149794-10-5

Usage

Uses

Used in Pharmaceutical Industry:
BOC-N-ETHYL GLYCINE is used as a building block for the synthesis of complex pharmaceutical compounds. Its application is primarily due to its ability to contribute to the development of potent, selective, and orally active peptide-based fibrinogen receptor antagonists, which have potential therapeutic applications in various medical conditions.
Used in Drug Design:
BOC-N-ETHYL GLYCINE is used as a key component in drug design, specifically for creating peptide-based fibrinogen receptor antagonists. The reason for its use in this application is its ability to enhance the potency, selectivity, and oral activity of the resulting pharmaceutical compounds, making them more effective and accessible for patients.

Upstream product

• 4530-20-5 BOC-glycine 
• 75-03-6 ethyl iodide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 623-33-6 glycine ethyl ester hydrochloride 
• 1249016-05-4 methyl N-(tert-butoxycarbonyl)-N-ethylglycinate 
• 6456-74-2 Glycine tert-butyl ester 
• 84532-85-4 methyl 2-(ethylamino)acetate 
• 22889-78-7 3,5-dichloro-4-aminopyridine 
• 98-80-6 phenylboronic acid 
• 627-01-0 N-ethylglycine 

Downstream Products

• 659734-30-2 [(5-chloro-2-methylphenylcarbamoyl)methyl]ethylcarbamic acid tert-butyl ester 
• 1121527-61-4 methyl N-ethylglycinate hydrochloride 
• 1229024-75-2 C₂₅H₂₈N₄O₂ 
• 1251583-74-0 C₃₂H₄₁ClN₄O₈ 
• 873581-31-8 N-Boc-N-cyclopropylmethyl-L-alanine 
• 1172579-70-2 (S)-2-amino-2-(4-methyltetrahydro-2H-pyran-4-yl)-N-(4-phenyl-1,2,3-thiadiazol-5-yl)acetamide 
• 1393122-07-0 Boc-N-EtGly-Gly-Phe-OtBu 

Relevant academic research and scientific papers

A Naphthalimide-Based Cd2+Fluorescent Probe with Carbamoylmethyl Groups Working as Chelators and PET-Promoters under Neutral Conditions

We have developed a novel naphthalimide-based Cd2+fluorescent probe (1), featuring almost no background response, high sensitivity and selectivity toward Cd2+through its high association constant [K=(2.10±0.423)×106], and a practical working pH range. Membrane-permeability was conferred on 1 by replacing the imide and amide substituents with n-butyl groups, and hence the derivative (4) has found practical utility on fluorescent imaging of Cd2+in HeLa cells. Comparison of fluorescent properties between various compounds derived from 1 has demonstrated that the carbamoylmethyl groups in 1 function not only as Cd2+chelators but also as promoters for photoinduced electron transfer (PET) by lowering the basicity of the two tertiary amino groups. As a result, 1 and 4 exhibited highly practical performance as Cd2+probes under neutral conditions.

Structural and thermodynamic characterization of temperature-dependent changes in the folding pattern of a synthetic triamide

Variable-temperature 1H NMR and IR studies of triamide 1 and related compounds indicate that 1 undergoes dramatic temperature-dependent conformational changes in relatively nonpolar solvents (methylene chloride and chloroform). The folding pattern favored at low temperatures in these chlorocarbons (1c) contains a single C=O?H-N hydrogen bond in a nine-membered ring, while a folding pattern containing only a six-membered-ring C=O?N-H interaction (1a) is favored at higher temperatures. Dimethyl sulfoxide, a very strong hydrogen-bond-accepting solvent, disrupts all internal hydrogen bonding in 1. Acetonitrile appears to disrupt the six-membered-ring hydrogen bond selectively and to promote nine-membered-ring interaction at room temperature, relative to chlorocarbon solvents. By treating the behavior of 1 as a two-state system, in which folding pattern 1c is considered to be the "native state" and all other folding patterns comprise the "denatured state", we have been able to carry out van't Hoff analyses of the temperature-dependent conformational changes. In methylene chloride, the native state is enthalpically preferred by 1.9-2.5 kcal/mol but entropically disfavored by 7.4-9.1 eu. Similar values are obtained in chloroform. This thermodynamic characterization demonstrates that, even in a relatively nonpolar environment, the relative enthalpic stabilities of alternative folding patterns cannot be predicted simply by maximizing the pairing of hydrogen-bond donors and acceptors.

HETEROARYL COMPOUNDS

Provided herein are compounds and pharmaceutical compositions comprising said compounds that are useful for treating cancers. Specific cancers include those that are mediated by YAP/TAZ or those that are modulated by the interaction between YAP/TAZ and TEAD.

IMIDAZOQUINOLINE-TYPE COMPOUNDS AND USES THEREOF

Provided in the present disclosure are imidazoquinoline-type compounds, methods for their preparation, pharmaceutical compositions thereof and their use, wherein the imidazoquinoline-type compounds, upon local administration, form depots inducing cell mediated immune response while mitigating a systemic proinflammatory immune response.

LOCALLY ACTING TOLL-LIKE RECEPTOR 7 (TLR7) AND/OR TLR8 AGONIST IMMUNOTHERAPY COMPOUNDS AND THEIR USES

Provided in the present disclosure are immunotherapy compounds, pharmaceutical compositions thereof and their use, wherein the immunotherapy compounds, upon local administration, form depots inducing cell mediated immune response while mitigating a systemic proinflammatory immune response.

Study of intramolecular aminolysis in peptides containing N-alkylamino acids at position 2

Many peptides and proteins, containing Nα-alkylamino acids (including proline) at the second position, are prone to intramolecular aminolysis (IA) with elimination of N-terminal dipeptide sequence as 2,5-diketopiperazines (DKP). We synthesized a series of short peptides, containing N-alkylamino acids at position 2, and studied their stability in the presence of acetic acid and amines. The presence of side chains in the second and the third amino acid residues and alkylation at Nα of the third amino acid residue slowed down IA. Nα-Alkyl residue in the first amino acid residue impeded IA only in peptides, containing three or more residues. Side chains of the first amino acids did not affect significantly the cleavage rates. Acetic acid promoted IA more strongly than aqueous ammonia, while tertiary amines were less effective. Peptides with methionine-S-oxide residues were more labile than the unoxidized analogs, suggesting intramolecular assistance of the S-oxide group in aminolysis. Surprisingly, intermediate compounds of the formula Boc-Met-MeXaa-Sar-NHR underwent rapid cleavage (endopeptolysis) upon attempted acidolytic deprotection.

INHIBITORS OF IAP

The invention provides novel inhibitors of IAP that are useful as therapeutic agents for treating malignancies where the compounds have the general formula (I), and G, X1, X2, R1, R2, R3, R4/sub

AZAINDOLE INHIBITORS OF IAP

The invention provides novel inhibitors of IAP that are useful as therapeutic agents for treating malignancies where the compounds have the general formula I: I wherein X1, X2, Y, Z1, Z2, Z3, Z4, R1, R2, R3, R3', R4, R4', R5, R6, R6' and R9 are as described herein.

Regioisomerism-dependent TLR7 agonism and antagonism in an imidazoquinoline

Chronic immune activation is a hallmark of progressive HIV infection. Recent reports point to the engagement of toll-like receptor 7 (TLR7) and -9 by viral RNA as contributing to the activation of innate immune responses, which drive viral replication leading to immune exhaustion. The only known class of TLR7 antagonists is single-stranded phosphorothioate oligonucleotides, which has been demonstrated to inhibit immune activation in human and Rhesus macaque in vitro models. The availability of a selective and potent small-molecule TLR7 antagonist should allow the evaluation of potential benefits of suppression of TLR7-mediated immune activation in HIV/AIDS. Gardiquimod is a known N1-substituted 1H-imidazoquinoline TLR7 agonist, the synthesis of which has not been published. We show that the 3H regioisomer is completely inactive as a TLR7 agonist and is weakly antagonistic. A des-amino precursor of the 3H regioisomer is more potent as a TLR7 antagonist, with an IC50 value of 7.5 μM. This class of compound may serve as a starting point for the development of small-molecule inhibitors of TLR7.

IMIDAZOPYRIDINE INHIBITORS OF IAP

The invention provides novel inhibitors of IAP that are useful as therapeutic agents for treating malignancies where the compounds have the general formula I: wherein Q, X1, X2, Y, Z R1, R2, R3, R3', R4, R4', R5, R6, R6' and n are as described herein.