Improved Total Synthesis of Tubulysins and Design, Synthesis, and Biological Evaluation of New Tubulysins with Highly Potent Cytotoxicities against Cancer Cells as Potential Payloads for Antibody-Drug Conjugates was written by Nicolaou, K. C.;Erande, Rohan D.;Yin, Jun;Vourloumis, Dionisios;Aujay, Monette;Sandoval, Joseph;Munneke, Stefan;Gavrilyuk, Julia. And the article was included in Journal of the American Chemical Society in 2018.Formula: C16H24N2O4 This article mentions the following:
Improved, streamlined total syntheses of natural tubulysins such as V and U, I (R = β-OH, β-OAc, resp.), and pretubulysin D I (R = H), and their application to the synthesis of designed tubulysin analogs, are described. Cytotoxicity evaluation of the synthesized compounds against certain cancer cell lines revealed a number of novel analogs with exceptional potencies [e.g., II: IC50 = 40 pM against MES SA (uterine sarcoma) cell line; IC50 = 6 pM against HEK 293T (human embryonic kidney cancer) cell line; and IC50 = 1.54 nM against MES SA DX (MES SA with marked multidrug resistance) cell line]. These studies led to a set of valuable structure-activity relationships that provide guidance to further mol. design, synthesis, and biol. evaluation studies. The extremely potent cytotoxic compounds discovered in these investigations are highly desirable as potential payloads for antibody-drug conjugates and other drug delivery systems for personalized targeted cancer chemotherapies. In the experiment, the researchers used many compounds, for example, (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9Formula: C16H24N2O4).
(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Formula: C16H24N2O4
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics