147252-84-4

Usage

Uses

Used in Pharmaceutical Industry:
N-BOC-D/L-ALANINOL is used as a key intermediate in the synthesis of heterocyclic compounds, which are essential in the development of various pharmaceuticals. These heterocyclic compounds have a wide range of applications, including the treatment of various diseases and disorders.
Used in Antiviral Applications:
N-BOC-D/L-ALANINOL is used as an integrase inhibiting antiviral agent, playing a crucial role in the development of medications to combat viral infections. Integrase inhibitors are a class of antiviral drugs that work by blocking the integration of viral DNA into the host cell's genome, thus preventing the virus from replicating and spreading.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 4799, 1981 DOI: 10.1021/jo00336a040

InChI:InChI=1/C8H17NO3/c1-6(5-10)9-7(11)12-8(2,3)4/h6,10H,5H2,1-4H3,(H,9,11)

Upstream product

• 35320-23-1 (R)-2-aminopropan-1-ol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 4530-20-5 BOC-glycine 
• 28875-17-4 (S)-N-(tert-butoxycarbonyl)alanine methyl ester 
• 117049-08-8 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl<(tert-butoxycarbonyl)amino>bromoacetate 
• 117681-86-4 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (tert-butoxycarbonyl)aminoacetate 
• 117049-10-2 2-tert-Butoxycarbonylamino-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 112392-66-2 methyl 2-{[(tert-butoxy)carbonyl]amino}propanoate 
• 6168-72-5 2-Amino-1-propanol 
• 147252-81-1 acetone O-(tert-butoxycarbonyl)oxime 
• 338-69-2 D-Alanine 
• 127407-54-9 (S)-2-t-butoxycarbonylamino-3-benzyloxy-1-methanesulfonyloxypropane 
• 79069-15-1 N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol 
• 23680-31-1 BOC-O-benzyl-L-serine 

Downstream Products

• 155768-90-4 2-[(R)-N-(tert-butyloxycarbonyl)amino]-1-phenoxypropane 
• 955399-15-2 [(1R)-2-methoxy-1-methylethyl]carbamic acid tert-butyl ester 
• 3744-87-4 Boc-(R)-Ala 
• 162684-55-1 2-chloro-N-{(R)-1-[5-phenyl-(1,2,4-triazol-3-yl)]thio-2-propyl}adenosine 
• 162684-54-0 2-chloro-N-[(R)-1-(4-phenyl-2-thiazolyl)thio-2-propyl]adenosine 
• 153293-98-2 methyl 4-[2(R)-amino-1-propoxy]phenylacetate 
• 1338090-90-6 [(R)-1-methyl-2-(3-trifluoromethylphenyl)ethyl]carbamic acid tert-butyl ester 
• 167421-83-2 tert-butyl N-[(1R)-1-methyl-2-phenylethyl]carbamate 
• 1000596-45-1 methyl (RS)-2-{2-[(tert-butoxycarbonyl)amino]propoxy}-3-methylbenzoate 
• 163120-56-7 1-(2-chloro-3-nitrophenoxy)propan-2-amine 
• 194156-54-2 Boc-2-methoxy-1-methyl-ethylamine 
• 1022954-68-2 tert-butyl ((1R)-2-{[4-formyl-1-(phenylsulfonyl)-1H-indol-5-yl]oxy}-1-methylethyl)carbamate 

Relevant academic research and scientific papers

Fluorinated Olefinic Lactams: The Case of Amino Acids - Preparation and Mechanistic Studies

Herein, we report the synthesis of analogues of amino acids with a monofluorovinyl moiety. Interestingly, we have found that cyclization of the obtained products proceeds easily in all cases. The cyclization process has not previously been observed at this reaction stage, and such fluorinated lactams derived from phenylalanine, valine, alanine have not been described before.

Urea based foldamers

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Exploring the dNTP -binding site of HIV-1 reverse transcriptase for inhibitor design

HIV-1 reverse transcriptase (RT) plays a central role in the viral life cycle, and roughly half of the FDA-approved anti-HIV drugs are targeting RT. Nucleoside analogs (NRTIs) require cellular phosphorylation for binding to RT, and to bypass this rate-limiting path, we designed a new series of acyclic nucleoside phosphonate analogs as nucleoside triphosphate mimics, aiming at the chelation of the catalytic Mg2+ ions via a phosphonate and/or a carboxylic acid group. Novel synthetic procedures were developed to access these nucleoside phosphonate analogs. X-ray structures in complex with HIV-1 RT/dsDNA demonstrated that their binding modes are distinct from that of our previously reported compound series. The impact of chain length, chirality and linker atom have been discussed. The detailed structural understanding of these new compounds provides opportunities for designing new class of HIV-1 RT inhibitors.

Synthesis of β-Phenethylamines via Ni/Photoredox Cross-Electrophile Coupling of Aliphatic Aziridines and Aryl Iodides

A photoassisted Ni-catalyzed reductive cross-coupling between tosyl-protected alkyl aziridines and commercially available (hetero)aryl iodides is reported. This mild and modular method proceeds in the absence of stoichiometric heterogeneous reductants and uses an inexpensive organic photocatalyst to access medicinally valuable β-phenethylamine derivatives. Unprecedented reactivity was achieved with the activation of cyclic aziridines. Mechanistic studies suggest that the regioselectivity and reactivity observed under these conditions are a result of nucleophilic iodide ring opening of the aziridine to generate an iodoamine as the active electrophile. This strategy also enables cross-coupling with Boc-protected aziridines.

HETEROCYCLIC COMPOUNDS

Provided herein are compounds of formula (I) which comprise a thiomorpholine 1,1-dioxide or 1-imino-thiomorpholine 1-oxide moiety, or pharmaceutically acceptable salts of any of the foregoing, pharmaceutical compositions that include a compound described herein (including salts of the compound) and methods of synthesizing the same. Also provided are methods of treating Hepatitis B viral (HBV) infections using a compound of formula (I), or pharmaceutically acceptable salts thereof.

NON-FUSED TRICYCLIC 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.

SHORT-ACTING BENZODIAZEPINE DERIVATIVES, PREPARATION METHOD THEREFOR, AND USE THEREOF

The present invention relates to a benzodiazepine derivative of Formula I as a short-acting anesthetic, a pharmaceutical composition comprising the same, a kit comprising the same, a preparation method thereof, an method of anesthesia using the same and use thereof in the manufacture of an anesthetic medicament.

Synthesis of Enantiomerically Pure 3-Substituted Piperazine-2-acetic Acid Esters as Intermediates for Library Production

The piperazine heterocycle is broadly exploited in FDA-approved drugs and biologically active compounds, but its chemical diversity is usually limited to ring nitrogen substitutions, leaving the four carbon atoms underutilized. Using an efficient six-step synthesis, chiral amino acids were transformed into 3-substituted piperazine-2-acetic acid esters as diastereomeric mixtures whose cis and trans products (dr 0.56 a? 2.2:1, respectively) could be chromatographically separated. From five amino acids (both antipodes) was obtained a complete matrix of 20 monoprotected chiral 2,3-disubstituted piperazines, each as a single absolute stereoisomer, all but one in multigram quantities. In keeping with our overall purpose of constructing more Csp3-enriched compound libraries for drug discovery, these diverse and versatile piperazines can be functionalized on either nitrogen atom, allowing them to be used as scaffolds for parallel library synthesis and as intermediates for the production of novel piperazine compounds.

PIPERIDINE DERIVATIVES AS INHIBITORS OF UBIQUITIN SPECIFIC PROTEASE 7

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Synthesis and biological evaluation of novel selective androgen receptor modulators (SARMs) Part III: Discovery of 4-(5-oxopyrrolidine-1-yl)benzonitrile derivative 2f as a clinical candidate

We previously reported that 4-(pyrrolidin-1-yl)benzonitrile derivative 1b was a selective androgen receptor modulator (SARM) that exhibited anabolic effects on organs such as muscles and the central nervous system (CNS), but neutral effects on the prostate. From further modification, we identified that 4-(5-oxopyrrolidine-1-yl)benzonitrile derivative 2a showed strong AR binding affinity with improved metabolic stabilities. Based on these results, we tried to enhance the AR agonistic activities by modifying the substituents of the 5-oxopyrrolidine ring. As a consequence, we found that 4-[(2S,3S)-2-ethyl-3-hydroxy-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile (2f) had ideal SARM profiles in Hershberger assay and sexual behavior induction assay. Furthermore, 2f showed good pharmacokinetic profiles in rats, dogs, monkeys, excellent nuclear selectivity and acceptable toxicological profiles. We also determined its binding mode by obtaining the co-crystal structures with AR.