185525-63-7

Usage

Uses

Used in Pharmaceutical Industry:
BOC-5-HYDROXY-DL-TRYPTOPHAN is used as a protecting group in peptide synthesis for the development of drugs targeting the central nervous system and mental health disorders. Its role in the synthesis process ensures that selective chemical reactions can occur, leading to the creation of effective peptide-based medications.
Used in Central Nervous System Drug Development:
BOC-5-HYDROXY-DL-TRYPTOPHAN is utilized as a key component in the development of drugs that target the central nervous system. Its protective properties during peptide synthesis contribute to the creation of medications that can potentially treat a range of mental health disorders.
Used in Mental Health Disorder Treatment:
BOC-5-HYDROXY-DL-TRYPTOPHAN is employed in the synthesis of drugs that address mental health disorders such as depression, anxiety, and insomnia. Its potential therapeutic benefits are attributed to its role in the development of peptide-based drugs that can modulate neurotransmitter levels and influence mood regulation.

Upstream product

• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 56-69-9 5-hydroxytryptophan 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1453-97-0 5-benzyloxygramine 
• 4350-09-8 L-5-HTP 

Downstream Products

• 917372-95-3 (S,S)-[1-[5-(4-acetylamino-phenoxy)-1H-indol-3-ylmethyl]-2-(2-cyano-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 917372-90-8 (S,S)-{2-(2-carbamoyl-pyrrolidin-1-yl)-1-[5-(4-nitro-phenoxy)-1H-indol-3-ylmethyl]-2-oxo-ethyl}-carbamic acid tert-butyl ester 
• 917373-17-2 (S,S)-4-{3-[2-tert-butoxycarbonylamino-3-(2-cyano-pyrrolidin-1-yl)-3-oxo-propyl]-1H-indol-5-yloxy}-benzoic acid 
• 917373-15-0 (S,S)-{2-(2-carbamoyl-pyrrolidin-1-yl)-1-{5-(4-formyl-phenoxy)-1H-indol-3-ylmethyl}-2-oxo-ethyl}-carbamic acid tert-butyl ester 
• 917372-91-9 (S,S)-{2-(2-cyano-pyrrolidin-1-yl)-1-[5-(4-nitro-phenoxy)-1H-indol-3-ylmethyl]-2-oxo-ethyl}-carbamic acid tert-butyl ester 
• 917373-16-1 (S,S)-{2-(2-cyano-pyrrolidin-1-yl)-1-{5-(4-formyl-phenoxy)-1H-indol-3-ylmethyl}-2-oxo-ethyl}-carbamic acid tert-butyl ester 
• 917372-94-2 (S,S)-[1-[5-(4-amino-phenoxy)-1H-indol-3-ylmethyl]-2-(2-cyano-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 53157-48-5 tert-butyl 2-(5-hydroxy-1H-indol-3-yl)ethylcarbamate 

Relevant academic research and scientific papers

Highly Efficient Activatable MRI Probe to Sense Myeloperoxidase Activity

Myeloperoxidase (MPO) is a key component of innate immunity but can damage tissues when secreted abnormally. We developed a new generation of a highly efficient MPO-activatable MRI probe (heMAMP) to report MPO activity. heMAMP has improved Gd stability compared to bis-5-HT-Gd-DTPA (MPO-Gd) and demonstrates no significant cytotoxicity. Importantly, heMAMP is more efficiently activated by MPO compared to MPO-Gd, 5HT-DOTA(Gd), and 5HT-DOTAGA-Gd. Molecular docking simulations revealed that heMAMP has increased rigidity via hydrogen bonding intramolecularly and improved binding affinity to the active site of MPO. In animals with subcutaneous inflammation, activated heMAMP showed a 2-3-fold increased contrast-to-noise ratio (CNR) compared to activated MPO-Gd and 4-10 times higher CNR compared to conventional DOTA-Gd. This increased efficacy was further confirmed in a model of unstable atherosclerotic plaque where heMAMP demonstrated a comparable signal increase and responsiveness to MPO inhibition at a 3-fold lower dosage compared to MPO-Gd, further underscoring heMAMP as a potential translational candidate.

HIGHLY EFFICIENT MYELOPEROXIDASE ACTIVATABLE IMAGING AGENTS

Provided herein are compounds useful as imaging agents. Exemplary compounds provided herein are useful as myeloperoxidase imaging agents using magnetic resonance or nuclear imaging techniques. Methods for preparing the compounds provided herein and diagnostic methods using the compounds are also provided.

MYELOPEROXIDASE IMAGING AGENTS

Provided herein are compounds useful as imaging agents. Exemplary compounds provided herein are useful as myeloperoxidase imaging agents using positron emission tomography or fluorescence imaging techniques. Methods for preparing the compounds provided herein and diagnostic methods using radiolabeled and unlabeled compounds are also provided.

Substrate Fragmentation for the Design of M. tuberculosis CYP121 Inhibitors

The cyclo-dipeptide substrates of the essential M. tuberculosis (Mtb) enzyme CYP121 were deconstructed into their component fragments and screened against the enzyme. A number of hits were identified, one of which exhibited an unexpected inhibitor-like binding mode. The inhibitory pharmacophore was elucidated, and fragment binding affinity was rapidly improved by synthetic elaboration guided by the structures of CYP121 substrates. The resulting inhibitors have low micromolar affinity, good predicted physicochemical properties and selectivity for CYP121 over other Mtb P450s. Spectroscopic characterisation of the inhibitors′ binding mode provides insight into the effect of weak nitrogen-donor ligands on the P450 heme, an improved understanding of factors governing CYP121–ligand recognition and speculation into the biological role of the enzyme for Mtb.

Synthesis of tryptophans by alkylation of chiral glycine enolate equivalents with quaternary gramines

Quaternary gramines were found to be a suitable source of the 3-methylindole fragment for diastereoselective alkylation. The best yields and stereoselectivity were obtained for the alkylation of a chiral William's morpholinone enolate. Based on this transformation, a general method for the synthesis of enantiopure, indole ring substituted tryptophan derivatives was developed with good overall yields.

Quantitative insight into the design of compounds recognized by the L-type amino acid transporter 1 (LAT1)

L-Type amino acid transporter 1 (LAT1) is a transmembrane protein expressed abundantly at the blood-brain barrier (BBB), where it ensures the transport of hydrophobic acids from the blood to the brain. Due to its unique substrate specificity and high expression at the BBB, LAT1 is an intriguing target for carrier- mediated transport of drugs into the brain. In this study, a comparative molecular field analysis (CoMFA) model with considerable statistical quality (Q2=0.53, R2=0.75, Q2 SE=0.77, R2 SE=0.57) and good external predictivity (CCC=0.91) was generated. The model was used to guide the synthesis of eight new prodrugs whose affinity for LAT1 was tested by using an in situ rat brain perfusion technique. This resulted in the creation of a novel LAT1 prodrug with l-tryptophan as the promoiety; it also provided a better understanding of the molecular features of LAT1-targeted high-affinity prodrugs, as well as their promoiety and parent drug. The results obtained will be beneficial in the rational design of novel LAT1-binding prodrugs and other compounds that bind to LAT1.

NOVEL 5-SUBSTITUTED INDOLE DERIVATIVES AS DIPEPTIDYL PEPTIDASE IV (DPP-IV) INHIBITORS

The present invention relates to 5-substituted indole derivatives of formula (I): having inhibitory potential of dipeptidyl peptidase IV (DPP IV) enzyme where x and R1 are defined as defined in the specification

Spiro piperidines and homologs promote release of growth hormone

There are disclosed certain novel compounds identified as spiro piperidines and homologs which promote the release of growth hormone in humans and animals. This property can be utilized to promote the growth of food animals to render the production of edible meat products more efficient, and in humans, to treat physiological or medical conditions characterized by a deficiency in growth hormone secretion, such as short stature in growth hormone deficient children, and to treat medical conditions which are improved by the anabolic effects of growth hormone. Growth hormone releasing compositions containing such spiro compounds as the active ingredient thereof are also disclosed.