195964-65-9

Usage

Uses

Used in Pharmaceutical Synthesis:
(2S)-5-Allyl-1,2-pyrrolidinedicarboxylic acid 1-(tert-butyl) 2-methyl ester serves as a key precursor in the synthesis of various pharmaceuticals and biologically active compounds. Its unique structural features and chirality contribute to the development of new drugs with potential therapeutic applications.
Used in Medicinal Chemistry Research:
As a chiral molecule with two stereoisomers, the (2S) isomer of (2S)-5-Allyl-1,2-pyrrolidinedicarboxylic acid 1-(tert-butyl) 2-methyl ester is more stable and prevalent, making it an important subject of study in medicinal chemistry. Researchers can explore its specific chemical and biological properties to advance the understanding of drug action and optimize drug candidates.
Used in Drug Design:
The addition of allyl and tert-butyl groups to the proline backbone of (2S)-5-Allyl-1,2-pyrrolidinedicarboxylic acid 1-(tert-butyl) 2-methyl ester endows the compound with distinct chemical properties that can be harnessed in drug design. Its enhanced lipophilicity allows for better cell membrane penetration, which is crucial for the effectiveness of many drugs.
Used in Biologically Active Compounds Synthesis:
(2S)-5-Allyl-1,2-pyrrolidinedicarboxylic acid 1-(tert-butyl) 2-methyl ester is also utilized in the synthesis of biologically active compounds, where its unique structural elements can contribute to the development of molecules with specific biological activities, potentially leading to new treatments and therapies.

Upstream product

• 195964-54-6 1-tert-butyl 2-methyl (2S)-5-methoxypyrrolidine-1,2-dicarboxylate 
• 762-72-1 allyl-trimethyl-silane 
• 24850-33-7 allyltributylstanane 
• 108963-96-8 (S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one 
• 1730-25-2 allylmagnesium bromide 
• 188200-05-7 1-(tertbutyloxycarbonyl)-5-(hydroxy)pyrrolidine-2-carboxylic acid methyl ester 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 67-56-1 methanol 
• 863660-29-1 benzyl (2S)-N-tert-butoxycarbonyl-5-allylpyrrolidine-2-carboxylate 
• 4931-66-2 methyl (S)-pyroglutamate 
• 98-79-3 L-Pyroglutamic acid 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 123457-52-3 (2S,5R)-5-allylpyrrolidine-1,2-dicarboxylic acid 1-benzylester 2-methylester 
• 210345-08-7 (5R,2S)-5-allyl-pyrrolidine-2-carboxylic acid methyl ester 
• 1071992-57-8 N1-[(5S,8S,10aR)-8-[N-(1,1-diphenylmethyl)carbamoyl]-3-(3-methylbutyryl)-6-oxoperhydropyrrolo[1,2-a][1,5]diazocin-5-yl]-N²-methyl-L-alaninamide hydrochloride 
• 1071993-04-8 C₁₆H₂₅N₃O₅ 
• 1296138-82-3 YP-348 
• 1191092-21-3 C₃₁H₄₀N₆O₄ 
• 1296138-88-9 C₃₉H₄₆N₆O₆ 
• 1296138-87-8 C₃₅H₃₉N₅O₅ 
• 1296138-86-7 C₃₅H₄₁N₅O₆ 
• 1296138-84-5 C₂₅H₃₇N₃O₈ 
• 1296138-83-4 YP-367 
• 957135-12-5 methyl (5S,8S,10aR)-5-[(tert-butoxycarbonyl)amino]-6-oxo-decahydro-1H-pyrrolo[1,2-a][1,5]diazocine-8-carboxylate 
• 210345-10-1 (2S,5R)-1-(2-Benzyloxy-3-phenyl-pent-4-enoyl)-5-vinyl-pyrrolidine-2-carboxylic acid methyl ester 
• 210345-13-4 (3S,9aR)-6-Benzyloxy-5-oxo-7-phenyl-2,3,5,6,7,9a-hexahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

A new spirocyclic proline-based lactam as efficient type II′ β-turn inducing peptidomimetic

A new proline-based spirotricyclic lactam is reported as an efficient type II′ β-turn inducing peptidomimetic. After investigations of the reverse turn properties by computational techniques, the scaffold has been synthesized by a straightforward sequence relying on a key RCM reaction for the construction of the spirocyclic lactams ring. For its conformational properties, the scaffold can be considered a privileged structure to be employed as a mimic of the β-turn motif of the potent antibiotic Gramicidin S.

Anodic substitution reaction of proline derivatives using the 2,4,6-trimethoxyphenyl leaving group

An efficient method for modifying a proline moiety through anodic carbon-carbon bond cleavage is developed. Use of the 2,4,6-trimethoxyphenyl (TMP) moiety as a leaving group at the 5-position allows the incorporation of various functional groups for modification in both the N- and C-terminal direction due to the stability of the N1-C5-C linkage. This approach also enables anodic substitution reactions using reactants with lower oxidation potential compared to N-carbonyl bonds.

COMPOUNDS USEFUL AS FACTOR XIA INHIBITORS

The present invention is directed to Factor XIa inhibitors, tautomers, stereoisomers, isotopologues, and pharmaceutically acceptable salts and solvates thereof, pharmaceutical compositions containing said compounds and the use of said compounds in the treatment and / or prophylaxis of thromboembolic disorders, inflammatory disorders, and diseases or conditions in which plasma kallikrein activity is implicated.

Debio-1143: Inhibitor of apoptosis protein (IAP) antagonist Cancer therapy

Inhibitors of apoptosis proteins (IAPs) block caspases, modulate nuclear factor NF-êB signaling pathways and are involved in resistance to cancer therapies. Debio-1143, a mimetic of an endogenous IAP inhibitor (second mitochondriaderived activator of caspases [SMAC]), may help to overcome treatment resistance and has demonstrated antitumor activity in various cancer cell lines and xenograft models, alone or in combination with chemotherapy, radiotherapy or immunotherapies. So far, about 150 cancer patients have been enrolled in 5 registered early-phase clinical trials testing Debio-1143. Tolerability was acceptable even when the drug was used in combination therapies. In monotherapy, pharmacokinetics was linear, but varied considerably among patients in combination settings. High tumor penetration and on-target activity were consistently shown in patient surrogate tissues and tumor biopsies. Tumor responses to second-(or higher) line monotherapy in patients with various advanced cancers were rather weak, but currently followed approaches as an adjunct to existing cancer therapies look encouraging. Still, to identify ideal target populations and concomitant regimens remains challenging.

Synthesis and evaluation of a (3R,6S,9S)-2-oxo-1-azabicyclo[4.3.0]nonane scaffold as a mimic of Xaa-trans-Pro in poly-l-proline type II helix conformation

We describe the development of a small-molecule mimic of Xaa-trans-Pro dipeptide in poly-l-proline type II helix conformation, based upon a (3R,6S,9S)-2-oxo-1-azabicyclo[4.3.0]nonane core structure. Stereoselective synthesis of the mimic from l-pyroglutamic acid is achieved in twelve linear steps and 9.9% yield. Configurational and conformational analyses are conducted using a combination of 1H NMR spectroscopy, X-ray crystallography and circular dichroism spectroscopy; and evaluation of the mimic as a promising surrogate dipeptide, in a protein-protein interaction between the SH3 domain of human Fyn kinase (Fyn SH3) and peptidomimetics of its biological ligand, are conducted by 1H-15N HSQC NMR titration experiments.

Synthesis of hydrophobic phase-tagged prolyl peptides featuring rapid reaction/separation

Hydrophobically tagged prolyl peptides were synthesized using an electrochemically modified prolyl moiety. The hydrophobic tag served a useful handle for the repetitive reaction/separation steps during solution-phase peptide synthesis. Furthermore, the ta

Stereoselective synthesis of 2,5-di- and 2,2,5-trisubstituted pyrrolidines by allylation reacton of acyliminium ion

-Allylation reactions of allytrimethylsilane and an allylcopper reagent to acyliminium ions derived from several 2-monosubstituted and 2,2-disubstituted pyrrolidinones were examined. These reactions proceeded in a stereoselective manner to give the corresponding allylated adducts. The stereochemical outcomes of these reactions were dependent upon the allylating reagents or the structures of the acyliminium ions.

Synthesis of new bicyclic lactam peptidomimetics by ring-closing metathesis reactions

An efficient and versatile synthetic method for the preparation of new fused bicyclic lactams 3a and 3b is described. The spirane cyclopentane nucleus was easily installed by diallylation of the pyroglutamate derivative 18 followed by ring-closing metathe

Novel interleukin-1beta converting enzyme inhibitors

The present invention relates to interleukin-1β converting enzyme inhibitors having the formula: R is a carbocyclic or heterocyclic ring; R1 is a cysteine trap; R2a, R2a′, R2b, and R2b are each independently hydrogen, C1-C4 alkyl, C1-C4 alkoxy, and mixtures thereof; or R2a′ and R2b′ can taken together to form a double bond; L and L1 are linking groups having the formula: T is selected from the group consisting of: i) —NR6—; ii) —O—; iii) —NR6S(O)2—; iv) —S(O)2NR6—; and v) mixtures thereof; R6 is hydrogen, substituted or unsubstituted C1-C20 linear, branched, or cyclic alkyl, C6-C20 aryl, C7-C20 alkylenearyl, and mixtures thereof; the indices w, w1, and w2 are each independently 0 or 1; i) hydrogen; ii) C1-C4 linear, branched, and cyclic alkyl; iii) R3a and R3b or R4a, and R4b can be taken together to form a carbonyl unit; iv) two R3a or two R3b units from adjacent carbon atoms or two R4a or two R4b units from adjacent carbon atoms can be taken together to form a double bond; and v) mixtures thereof; the index m is from 0 to 5; the index n is from 0 to 5.

Stereoselective bromination-suzuki cross-coupling of dehydroamino acids to form novel reverse-turn peptidomimetics: substituted unsaturated and saturated indolizidinone amino acids.

A general and efficient methodology has been developed to prepare the C4-substituted dipeptide reverse-turn mimetics unsaturated (9a, 10a) and saturated (11a) azabicyclo[4.3.0] alkane amino acid derivatives. The side chain was introduced by bromination of