scholarly journals Synthesis of 2-aminosuberic acid derivatives as components of some histone deacetylase inhibiting cyclic tetrapeptides

2017 ◽  
Vol 13 ◽  
pp. 2153-2156 ◽  
Author(s):  
Shital Kumar Chattopadhyay ◽  
Suman Sil ◽  
Jyoti Prasad Mukherjee
Keyword(s):  
Amino Acid ◽  
Histone Deacetylase ◽  
Building Block ◽  
Suberic Acid ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
Important Amino Acid ◽  
New Synthesis ◽  
Cyclic Tetrapeptides ◽  
Derivatives Of

A new synthesis of the important amino acid 2-aminosuberic acid from aspartic acid is reported. The methodology involves the alternate preparation of (S)-2-aminohept-6-enoate ester as a building block and its diversification through a cross-metathesis reaction to prepare the title compounds. The utility of the protocol is demonstrated through the preparation of three suberic acid derivatives of relevance to the design and the synthesis of peptides of biological relevance.

scholarly journals α,ß-Didehydrosuberoylanilide hydroxamic acid (DDSAHA) as precursor and possible analogue of the anticancer drug SAHA

2019 ◽  
Vol 15 ◽  
pp. 2524-2533 ◽  
Author(s):  
Shital K Chattopadhyay ◽  
Subhankar Ghosh ◽  
Sarita Sarkar ◽  
Kakali Bhadra
Keyword(s):  
Anticancer Drug ◽  
Hela Cells ◽  
Hydroxamic Acid ◽  
Suberoylanilide Hydroxamic Acid ◽  
Oxygen Species ◽  
Synthetic Route ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
Terminal Alkene ◽  
Derivatives Of

An alternate synthetic route to the important anticancer drug suberoylanilide hydroxamic acid (SAHA) from its α,ß-didehydro derivative is described. The didehydro derivative is obtained through a cross metathesis reaction between a suitable terminal alkene and N-benzyloxyacrylamide. Some of the didehydro derivatives of SAHA were preliminarily evaluated for anticancer activity towards HeLa cells. The administration of the analogues caused a significant decrease in the proliferation of HeLa cells. Furthermore, one of the analogues showed a maximum cytotoxicity with a minimum GI50 value of 2.5 µg/mL and the generation of reactive oxygen species (ROS) as some apoptotic features.

scholarly journals Halogen effects on the solid-state packing of phenylalanine derivatives and the resultant gelation properties

2017 ◽  
Vol 203 ◽  
pp. 423-439 ◽  
Author(s):  
Susana M. Ramalhete ◽  
Jamie S. Foster ◽  
Hayley R. Green ◽  
Karol P. Nartowski ◽  
Margaux Heinrich ◽  
...  
Keyword(s):  
Amino Acid ◽  
Solid State ◽  
Human Health ◽  
Crystal Structures ◽  
Aromatic Ring ◽  
Building Block ◽  
Artificial Sweeteners ◽  
Aromatic Group ◽  
Important Amino Acid

Phenylalanine is an important amino acid both biologically, essential to human health, and industrially, as a building block of artificial sweeteners. Our interest in this particular amino acid and its derivatives lies with its ability to form gels in a number of solvents. We present here the studies of the influence of halogen addition to the aromatic ring on the gelation properties and we analyse the crystal structures of a number of these materials to elucidate the trends in their behaviour based on the halogen addition to the aromatic group and the interactions that result.

Preparation of Boc-Protected Cinnamyl-Type Alcohols: A Comparison of the Suzuki-Miyaura Coupling, Cross-Metathesis, and Horner-Wadsworth-Emmons Approaches and Their Merit in Parallel Synthesis

2008 ◽  
Vol 73 (5) ◽  
pp. 705-732 ◽  
Author(s):  
Jan Štambaský ◽  
Andrei V. Malkov ◽  
Pavel Kočovský
Keyword(s):  
High Throughput ◽  
Building Block ◽  
Coupling Reaction ◽  
Parallel Synthesis ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
One Step ◽  
Purification Protocol

Three synthetic strategies for the construction of tert-butyl (E)-3-arylprop-2-en-1-ol carbonates are described. Complementary approaches employing Suzuki-Miyaura coupling and cross-metathesis reaction gave moderate yields of the title compounds in one-step, both methods are suitable for high-throughput and parallel chemistry. A detailed investigation into the Suzuki-Miyaura coupling reaction is provided along with the studies on the synthesis of pinacolyl 1-(tert-butyloxycarbonyl)propenol-3-ylboronate, the key building block. Conventional synthesis of the title compounds via the Horner-Wadsworth-Emmons reaction as a key step in a three-step-one-purification protocol was optimized and the results are compared with those of the latter reactions.

Three Amino Acid Derivatives of Valproic Acid: Design, Synthesis, Theoretical and Experimental Evaluation as Anticancer Agents

2014 ◽  
Vol 14 (7) ◽  
pp. 984-993 ◽  
Author(s):  
Gabriela Luna-Palencia ◽  
Federico Martinez-Ramos ◽  
Ismael Vasquez-Moctezuma ◽  
Manuel Fragoso-Vazquez ◽  
Jessica Mendieta-Wejebe ◽  
...  
Keyword(s):  
Valproic Acid ◽  
Amino Acid ◽  
Anticancer Agents ◽  
Experimental Evaluation ◽  
Amino Acid Derivatives ◽  
Design Synthesis ◽  
Derivatives Of

Quantitative helix handedness bias through a single H vs. CH3 stereochemical differentiation

2021 ◽  
Author(s):  
Daniel Bindl ◽  
Elisabeth Heinemann ◽  
Pradeep Kumar Mandal ◽  
Ivan Huc
Keyword(s):  
Amino Acid ◽  
Building Block

A novel chiral aromatic δ-amino acid building block was shown to fully induce handedness in quinoline oligoamide foldamers with the possibility to further increase the bias by combining multiple of...

scholarly journals Novel Amino Acid Derivatives of Quinolines as Potential Antibacterial and Fluorophore Agents

2020 ◽  
Vol 88 (4) ◽  
pp. 57
Author(s):  
Oussama Moussaoui ◽  
Rajendra Bhadane ◽  
Riham Sghyar ◽  
El Mestafa El Hadrami ◽  
Soukaina El Amrani ◽  
...  
Keyword(s):  
Amino Acid ◽  
Methyl Esters ◽  
Amino Acid Derivatives ◽  
Bacterial Strains ◽  
Fluorescent Properties ◽  
Topoisomerase Iv ◽  
Microdilution Method ◽  
Hydrolysis Of ◽  
Derivatives Of

A new series of amino acid derivatives of quinolines was synthesized through the hydrolysis of amino acid methyl esters of quinoline carboxamides with alkali hydroxide. The compounds were purified on silica gel by column chromatography and further characterized by TLC, NMR and ESI-TOF mass spectrometry. All compounds were screened for in vitro antimicrobial activity against different bacterial strains using the microdilution method. Most of the synthesized amino acid-quinolines show more potent or equipotent inhibitory action against the tested bacteria than their correspond esters. In addition, many of them exhibit fluorescent properties and could possibly be utilized as fluorophores. Molecular docking and simulation studies of the compounds at putative bacterial target enzymes suggest that the antimicrobial potency of these synthesized analogues could be due to enzyme inhibition via their favorable binding at the fluoroquinolone binding site at the GyrA subunit of DNA gyrase and/or the ParC subunit of topoisomerase-IV.

Synthesis of Some Amino Acid Derivatives of Styrene1

1959 ◽  
Vol 81 (2) ◽  
pp. 377-382 ◽  
Author(s):  
L. R. Morris ◽  
R. A. Mock ◽  
C. A. Marshall ◽  
J. H. Howe
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Derivatives Of
Sign in / Sign up

Export Citation Format

Share Document