162465-45-4

Usage

Uses

Used in Pharmaceutical Industry:
(R)-2-((tet-butoxycarbonyl)amino)-3-(3-chloro-4-methoxyphenyl)propanoic acid is used as a building block for the synthesis of pharmaceutical compounds due to its unique structural features and reactivity. The presence of the protected amino group and the 3-chloro-4-methoxyphenyl substituent allows for the creation of a variety of biologically active molecules with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, (R)-2-((tet-butoxycarbonyl)amino)-3-(3-chloro-4-methoxyphenyl)propanoic acid serves as an essential intermediate for the preparation of complex organic molecules. Its structural components facilitate selective reactions and functional group manipulations, making it a valuable asset in the synthesis of target compounds with specific properties and functions.
Used in Peptide Synthesis:
(R)-2-((tet-butoxycarbonyl)amino)-3-(3-chloro-4-methoxyphenyl)propanoic acid is used as a key component in peptide synthesis. The protected amino group allows for the controlled formation of peptide bonds, while the 3-chloro-4-methoxyphenyl substituent can influence the overall properties of the resulting peptides, potentially enhancing their stability, selectivity, or biological activity.
Used in Research and Development:
(R)-2-((tet-butoxycarbonyl)amino)-3-(3-chloro-4-methoxyphenyl)propanoic acid is also utilized in research and development settings to study the effects of structural modifications on the reactivity and biological activity of molecules. The 3-chloro-4-methoxyphenyl group and the protected amino functionality provide a platform for exploring structure-activity relationships and optimizing the properties of novel compounds for various applications.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 478183-57-2 (2R)-2-[(tert-butoxycarbonyl)amino]-3-(3-chloro-4-hydroxyphenyl)propanoic acid 
• 556-02-5 tyrosine 
• 70601-62-6 (D)-N-acetyl-4-methoxy-phenylalanine 
• 162465-44-3 methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-(3-chloro-4-methoxyphenyl)propanoate 

Downstream Products

• 182486-23-3 (S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid allyl ester 
• 1196466-53-1 (R)-tert-butyl 1-(3-chloro-4-methoxyphenyl)-4-diazo-3-oxobutan-2-ylcarbamate 
• 186256-68-8 cryptophycin 53 
• 186256-69-9 cryptophycin 55 
• 186256-67-7 cryptophycin 52 

Relevant academic research and scientific papers

Cryptophycin-55/52 based antibody-drug conjugates: Synthesis, efficacy, and mode of action studies

Cryptophycin-52 (CR52), a tubulin inhibitor, exhibits promising antitumor activity in vitro (picomolar level) and in mouse xenograft models. However, the narrow therapeutic window in clinical trials limits its further development. Antibody-drug conjugate (ADC), formed by coupling cytotoxic compound (payload) to an antibody via a linker, can deliver drug to tumor locations in a targeted manner by antibody, enhancing the therapeutic effects and reducing toxic and side effects. In this study, we aim to explore the possibility of CR52-based ADC for tumor targeted therapy. Due to the lack of a coupling site in CR52, its prodrug cryptophycin-55 (CR55) containing a free hydroxyl was synthesized and conjugated to the model antibody trastuzumab (anti-HER2 antibody drug approved by FDA for breast cancer therapy) via the linkers based on Mc-NHS and Mc-Val-Cit-PAB-PNP. The average drug-to-antibody ratios (DARs) of trastuzumab-CR55 conjugates (named T-L1-CR55, T-L2-CR55, and T-L3-CR55) were 3.50, 3.29, and 3.35, respectively. These conjugates exhibited potent cytotoxicity in HER2-positive tumor cell lines with IC50 values at low nanomolar levels (0.58–1.19 nM). Further, they displayed significant antitumor activities at the doses of 10 mg/kg in established ovarian cancer (SKOV3) and gastric cancer (NCI–N87) xenograft models without overt toxicities. Finally, the drug releases were analyzed and the results indicated that T-L3-CR55 was able to effectively release CR55 and further epoxidized to CR52, which may be responsible for its best performance in antitumor activities. In conclusion, our results demonstrated that these conjugates have the potential for tumor targeted therapy, which provides insights to further research the CR55/CR52-based ADC for tumor therapy.

NOVEL CRYPTOPHYCIN COMPOUNDS AND CONJUGATES, THEIR PREPARATION AND THEIR THERAPEUTIC USE

The present invention relates to cryptophycin compounds of formula (I). The invention also relates to cryptophycin payloads, to cryptophycin conjugates, to compositions containing them and to their therapeutic use, especially as anticancer agents. The inv

Total Synthesis of Cryptophycins-1, -3, -4, -24 (Arenastatin A), and -29, Cytotoxic Depsipeptides from Cyanobacteria of the Nostocaceae

A convergent synthesis of cryptophycins has been developed in which (5S,6R)-5-hydroxy-6-methyl-8-phenylocta-2(E),7(E)-dienoic acid (A) is coupled with an amino acid segment (B). Two stereo-selective routes to A are described, the first employing allylatio

Total synthesis of cryptophycins. Revision of the structures of cryptophycins A and C

The convergent total synthesis of cryptophycins C and D is described. It has been shown that in both natural products the absolute configuration of the α-amino acid corresponds to the D-series. The structural assignment for cryptophycin C has been correct