49759-74-2

Usage

Uses

Used in Chemical Research and Experimentation:
Tert-Butyl [(1S)-1-(hydrazinocarbonyl)-3-(methylthio)propyl]carbamate is used as a research chemical for its unique structural features, contributing to the understanding of chemical reactions and mechanisms involving carbamate and related functional groups.
Used in Pharmaceutical Research:
In the pharmaceutical industry, tert-Butyl [(1S)-1-(hydrazinocarbonyl)-3-(methylthio)propyl]carbamate is used as a precursor or intermediate in the synthesis of new drugs. Its specific functional groups may offer novel pathways for drug development, targeting various therapeutic areas.

Upstream product

• 75-44-5 phosgene 
• 2491-18-1 (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride 
• 75-65-0 tert-butyl alcohol 
• 33900-24-2 N-(tert-butoxycarbonyl)-L-methionine methyl ester 

Downstream Products

• 112372-57-3 Boc-Met-Glu(OBzl)-OH 
• 1194046-35-9 C₂₁H₃₂N₄O₅S₂ 
• 109453-37-4 N-L-methionyl-L-glutamic acid-5-benzyl ester 

Relevant academic research and scientific papers

Amino Acid Functionalized Organotin Trichlorides and Their Tin Sulfide Clusters

We present a new synthesis of functionalized tin sulfide clusters via organotin trichlorides with boc-protected amino acids (RAAcSnCl3). In this work we used non-polar (alanine, valine, leucine, phenylalanine and methionine), polar/neutral (serine and tyrosine) and basic (histidine) amino acids. We obtained single crystals from a Boc-protected valine derivative of the originally used organotin trichloride R1SnCl3 [R1 = CMe2CH2C(O)Me] and determined its structure by means of X-ray diffraction. A subsequent reaction with sulfide sources led to a variety of respective cluster structures. By using either (Me3Si)2S or Na2S, the reaction product turns out to be the defect-heterocubane cluster [(RAAcSn)3S4Cl] or the “doppeldecker”-type cluster [(RAAcSn)4S6], respectively, according to 119Sn NMR spectroscopy.

Synthesis of 5 H -Pyrrolo[3,4- b ]pyrazine-Based Peptidomimetics

A range of 5H-pyrrolo[3,4-b]pyrazine-based peptidomimetics were designed, and their efficient synthesis starting from 5-imino-5H-pyrrolo[3,4-b]pyrazin-7-amine by subsequent interaction with N-protected amino acid hydrazides and amino acid esters with N,N-carbonyldiimidazole as the coupling agent was elaborated.

Design, synthesis and biological evaluation of a library of thiocarbazates and their activity as cysteine protease inhibitors

Recently, we identified a novel class of potent cathepsin L inhibitors, characterized by a thiocarbazate warhead. Given the potential of these compounds to inhibit other cysteine proteases, we designed and synthesized a library of thiocarbazates containing diversity elements at three positions. Biological characterization of this library for activity against a panel of proteases indicated a significant preference for members of the papain family of cysteine proteases over serine, metallo-, and certain classes of cysteine proteases, such as caspases. Several potent inhibitors of cathepsin L and S were identified. The SAR data were employed in docking studies in an effort to understand the structural elements required for cathepsin S inhibition. This study provides the basis for the design of highly potent and selective inhibitors of the papain family of cysteine proteases.