848777-30-0

Basic information

• Product Name: (S)-2-cyclohexyl-2-(pyrazine-2-carboxaMido)acetic acid
• Synonyms: (S)-2-cyclohexyl-2-(pyrazine-2-carboxaMido)acetic acid;Cyclohexaneacetic acid, a-[(pyrazinylcarbonyl)aMino]-, (aS)-;(2S)-Cyclohexyl[(2-pyrazinylcarbonyl)aMino]acetic acid;(alphaS)-alpha-[(Pyrazinylcarbonyl)amino]cyclohexaneacetic acid;Cyclohexaneacetic acid,alpha-[(2-pyrazinylcarbonyl)aMino]-, (S)-;Cyclohexaneaceticacid,a-[(2-pyrazinylcarbonyl)aMino]-,(S)-;(2S)-2-cyclohexyl-2-(pyrazine-2-carbonylamino)acetic acid
• CAS NO: 848777-30-0
• Molecular Formula: C₁₃H₁₇N₃O₃
• Molecular Weight: 266.3162
• Mol File: 848777-30-0.mol

Chemical Properties

• Boiling Point: 549.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.266
• PKA: 3.09±0.10(Predicted)
• CAS DataBase Reference: (S)-2-cyclohexyl-2-(pyrazine-2-carboxaMido)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-cyclohexyl-2-(pyrazine-2-carboxaMido)acetic acid(848777-30-0)
• EPA Substance Registry System: (S)-2-cyclohexyl-2-(pyrazine-2-carboxaMido)acetic acid(848777-30-0)

Safety Data

• Hazardous Substances Data: 848777-30-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetic acid is utilized as a research compound for exploring its potential in the development of new pharmaceutical agents. Its unique structure and functional groups may contribute to the discovery of novel therapeutic agents with specific biological activities.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetic acid serves as a key building block or intermediate in the synthesis of complex organic molecules with potential medicinal properties. Its incorporation into various chemical frameworks can lead to the creation of new drug candidates with improved pharmacological profiles.
Used in Chemical Synthesis:
(S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetic acid is employed as a versatile synthetic intermediate in the preparation of a wide range of chemical compounds. Its reactive functional groups facilitate various chemical reactions, enabling the synthesis of diverse organic molecules for use in different industries.
Used in Analytical Chemistry:
As a chiral compound, (S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetic acid can be used in analytical chemistry for the development of enantioselective methods and techniques. Its presence in samples can be detected and quantified using chiral chromatography, providing valuable insights into the stereochemistry of complex mixtures.
Used in Material Science:
The unique structural features of (S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetic acid may also find applications in material science, where it can be used to design and synthesize novel materials with specific properties. Its incorporation into polymers, for instance, could lead to the development of new materials with tailored characteristics for various applications.

InChI:InChI=1S/C13H17N3O3/c17-12(10-8-14-6-7-15-10)16-11(13(18)19)9-4-2-1-3-5-9/h6-9,11H,1-5H2,(H,16,17)(H,18,19)/t11-/m0/s1

Upstream product

• 848777-29-7 (S)-methyl 2-cyclohexyl-2-(pyrazine-2-carboxamido)acetate 
• 98-97-5 2-pyrazylcarboxylic acid 
• 145618-11-7 (S)-amino(cyclohexyl)acetic acid methyl ester 
• 1454838-80-2 L-α-cyclohexylglycine potassium salt 
• 14328-63-3 methyl (2S)-amino(cyclohexyl)ethanoate hydrochloride 

Downstream Products

• 856707-36-3 C₂₈H₄₁N₅O₅ 
• 856707-70-5 C₃₃H₄₁N₅O₅ 
• 402959-36-8 (1S,3aR,6aS)-2-[(2S)-2-[[(2S)-2-cyclohexyl-2-[(2-pyrazinylcarbonyl)amino] acetyl]amino]-3,3-dimethylbutanoyl]-N-[(1S)-1-[(cyclopropylamino)(hydroxy)acetyl]butyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-3-carboxamide 
• 1257874-86-4 C₃₈H₅₇N₇O₇ 
• 402958-96-7 (S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoic acid 
• 402957-28-2 (1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide 
• 402958-95-6 (S)-methyl 2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoate 
• 1033882-68-6 (3R,4R)-di-tert-butyl 4-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-N,3,3-trimethylbutanamido)pyrrolidine-1,3-dicarboxylate 
• 1033881-93-4 (S)-tert-butyl 2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3-methylbutanoate 
• 1033882-37-9 (S)-tert-butyl 2-cyclohexyl-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)acetate 
• 1033882-44-8 (S)-tert-butyl 2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)pentanoate 
• 1033881-87-6 (S)-tert-butyl 2-(2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)acetate 
• 1033882-51-7 (S)-tert-butyl 2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-4-methylpentanoate 
• 1208119-14-5 C₂₂H₃₃N₅O₆ 

Relevant articles and documents

Development of peptidomimetic hydroxamates as PfA-M1 and PfA-M17 dual inhibitors: Biological evaluation and structural characterization by cocrystallization

Plasmodium parasites causing malaria have developed resistance to most of the antimalarials in use, including the artemisinin-based combinations, which are the last line of defense against malaria. This necessitates the discovery of new targets and the development of novel antimalarials. Plasmodium falciparum alanyl aminopeptidase (PfA-M1) and leucyl aminopeptidase (PfA-M17) belong to the M1 and M17 family of metalloproteases respectively and play critical roles in the asexual erythrocytic stage of development. These enzymes have been suggested as potential antimalarial drug targets. Herein we describe the development of peptidomimetic hydroxamates as PfA-M1 and PfA-M17 dual inhibitors. Most of the compounds described in this study display inhibition at sub-micromolar range against the recombinant PfA-M1 and PfA-M17. More importantly, compound 26 not only exhibits potent malarial aminopeptidases inhibitory activities (PfA-M1 Ki = 0.11 ± 0.0002 μmol/L, PfA-M17 Ki = 0.05 ± 0.005 μmol/L), but also possesses remarkable selectivity over the mammalian counterpart (pAPN Ki = 17.24 ± 0.08 μmol/L), which endows 26 with strong inhibition of the malarial parasite growth and negligible cytotoxicity on human cell lines. Crystal structures of PfA-M1 at atomic resolution in complex with four different compounds including compound 26 establish the structural basis for their inhibitory activities. Notably, the terminal ureidobenzyl group of 26 explores the S2′ region where differences between the malarial and mammalian enzymes are apparent, which rationalizes the selectivity of 26. Together, our data provide important insights for the rational and structure-based design of selective and dual inhibitors of malarial aminopeptidases that will likely lead to novel chemotherapeutics for the treatment of malaria.

PROCESS FOR THE PREPARATION OF INTERMEDIATES USEFUL IN THE PREPARATION OF A VIRAL PROTEASE INHIBITOR

Process for the preparation of intermediates useful in the synthesis of the viral protease inhibitor Telaprevir. The claimed process involves reacting formula (IV) with a formula (III) compound using DMMTM as coupling reagent to get a formula (II) compoun

A PROCESS FOR THE PREPARATION OF SUBSTITUTED PROLYL PEPTIDES AND SIMILAR PEPTIDOMIMETICS

The present invention relates to a process for the stereoselective preparation of a compound having the general formula (I) or its respective diastereomers: comprising reacting a compound having the general formula (II) or its diastereomers: with a compound of the general formula III: R3-COOH and a compound of the general formula IV: R4-NC wherein R1 represents each independently, or jointly a substituted or unsubstituted alkyl, alkenyl, alkynyl, aromatic or non-aromatic, mono-, di- or tricyclic, or heterocyclic structure, and R2 represents a hydrogen atom, a substituted or unsubstituted alkyl, alkenyl, alkynyl, aromatic or non-aromatic, mono-, di- or tricyclic, or heterocyclic structure, and R3 represents a substituted or unsubstituted alkyl, alkenyl, or alkynyl, or an aromatic or non-aromatic aromatic or non-aromatic, mono-, di- or tricyclic, or heterocyclic structure.

Chemical and biological evaluation of dipeptidyl boronic acid proteasome inhibitors for use in prodrugs and pro-soft drugs targeting solid tumors

Bortezomib, a dipeptidyl boronic acid and potent inhibitor of the 26S proteasome, is remarkably effective against multiple myeloma (MM) but not against solid tumors. Dose-limiting adverse effects from "on target" inhibition of the proteasome in normal cells and tissues appear to be a key obstacle. Achieving efficacy against solid tumors therefore is likely to require making the inhibitor more selective for tumor tissue over normal tissues. The simplest strategy that might provide such tissue specificity would be to employ a tumor specific protease to release an inhibitor from a larger, noninhibitory structure. However, such release would necessarily generate an inhibitor with a free N-terminal amino group, raising a key question: Can short peptide boronic acids with N-terminal amino groups have the requisite properties to serve as warheads in prodrugs? Here we show that dipeptides of boroLeu, the smallest plausible candidates for the task, can indeed be sufficiently potent, cell-penetrating, cytotoxic, and stable to degradation by cellular peptidases to serve in this capacity.

A highly efficient synthesis of telaprevir by strategic use of biocatalysis and multicomponent reactions

A very short and efficient synthesis of the important drug candidate telaprevir, featuring a biocatalytic desymmetrization and two multicomponent reactions as the key steps, is presented. The classical issue of lack of stereoselectivity in Ugi- and Passerini-type reactions is circumvented. The atom economic and convergent nature of the synthetic strategy require only very limited use of protective groups.

HCV PROTEASE INHIBITORS AND USES THEREOF

This invention relates to: (a) compounds of formula I and salts thereof that, inter alia, are useful as hepatitis C virus (HCV) inhibitors; (b) intermediates useful for the preparation of such compounds and salts; (c) pharmaceutical compositions comprising such compounds and salts; and (d) methods of use of such compounds, salts, and compositions.

HCV PROTEASE INHIBITORS AND USES THEREOF

The present invention provides compounds, pharmaceutically acceptable compositions thereof, and methods of using the same.

Pharmaceutical formulations and methods of treatment using the same

Pharmaceutical formulations containing at least one compound of Formulae I-XXVI herein and at least one surfactant. Pharmaceutically acceptable carriers and excipients may also be included in the formulations. The formulations of the present invention are suited for use in single unit dosages.

Liver/plasma concentration ratio for dosing hepatitis C virus protease inhibitor

Compositions and therapeutic combinations are provided including at least one compound selected from the group consisting of compounds of Formulae I to XXVI as defined herein as well as methods of treatment, prevention or amelioration of one or more symptoms of hepatitis C, treating disorders associated with HCV virus, modulating activity of HCV protease, in which liver to plasma concentration ratio of the compound ranges from about 2:1 to about 10:1.

ORGANIC COMPOUNDS AND THEIR USES

The present application describes organic compounds that are useful for the treatment, prevention and/or amelioration of human diseases.