936691-46-2

Basic information

• Product Name: C₃₈H₅₇N₅O₇S
• CAS NO: 936691-46-2
• Molecular Weight: 727.966
• Mol File: 936691-46-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 904.9±65.0 °C(Predicted)
• Density: 1.171±0.06 g/cm3(Predicted)
• CAS DataBase Reference: C₃₈H₅₇N₅O₇S(CAS DataBase Reference)
• NIST Chemistry Reference: C₃₈H₅₇N₅O₇S(936691-46-2)
• EPA Substance Registry System: C₃₈H₅₇N₅O₇S(936691-46-2)

Safety Data

• Hazardous Substances Data: 936691-46-2(Hazardous Substances Data)

Usage

Uses

Tubulysin M is a Tubulysin D analog with potential anti-cancer properties. Inhibitor of cell-growth, acts as a cytotoxic agent.

Upstream product

• 50-00-0 formaldehyd 
• 2174-58-5 L-malic acid 
• 6973-20-2 (S)-methylsuccinic anhydride 
• 1207472-62-5 (S,E)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpent-2-enoate 
• 356788-71-1 [L-(trans)]-4-[(t-butoxycarbonyl)amino]-2-methyl-5-phenyl-2-pentenoic acid 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 244033-72-5 (4S)-4-N-tert-butoxycarbonylamino-5-phenyl-2-methyl-2-trans-pentenoic acid, ethyl ester 
• 72155-45-4 Boc-L-phenylalaninal 
• 108-24-7 acetic anhydride 

Relevant articles and documents

Design, Synthesis, and Cytotoxic Evaluation of Novel Tubulysin Analogues as ADC Payloads

The tubulysin class of natural products has attracted much attention from the medicinal chemistry community due to its potent cytotoxicity against a wide range of human cancer cell lines, including significant activity in multidrug-resistant carcinoma models. As a result of their potency, the tubulysins have become an important tool for use in targeted therapy, being widely pursued as payloads in the development of novel small molecule drug conjugates (SMDCs) and antibody-drug conjugates (ADCs). A structure-based and parallel medicinal chemistry approach was applied to the synthesis of novel tubulysin analogues. These efforts led to the discovery of a number of novel and potent cytotoxic tubulysin analogues, providing a framework for our simultaneous report, which highlights the discovery of tubulysin-based ADCs, including use of site-specific conjugation to address in vivo stability of the C-11 acetate functionality.

TUBULYSIN DERIVATIVES AND METHODS FOR PREPARING THE SAME

The invention relates to novel means and methods for the synthesis of tubulysin and derivatives thereof, which find their use e.g. as cytotoxic agents in targeted drug delivery. Provided is a method for preparing a tubulysin derivative, comprising reacting compounds A, B and C in a 3- component Passerini reaction, wherein compound A is a carboxylic acid according to the general formula (A); wherein compound B is an aldehyde according to the general formula (B); and wherein compound C is an isocyanide according to the general formula (C).

Total Synthesis and Biological Evaluation of Natural and Designed Tubulysins

A streamlined total synthesis of N14-desacetoxytubulysin H (Tb1) based on a C-H activation strategy and a short total synthesis of pretubulysin D (PTb-D43) are described. Applications of the developed synthetic strategies and technologies to the synthesis of a series of tubulysin analogues (Tb2-Tb41 and PTb-D42) are also reported. Biological evaluation of the synthesized compounds against an array of cancer cells revealed a number of novel analogues (e.g., Tb14), some with exceptional potencies against certain cell lines [e.g., Tb32 with IC50 = 12 pM against MES SA (uterine sarcoma) cell line and 2 pM against HEK 293T (human embryonic kidney) cell line], and a set of valuable structure-activity relationships. The highly potent cytotoxic compounds discovered in this study are highly desirable as payloads for antibody-drug conjugates and other drug delivery systems for personalized targeted cancer chemotherapies.