1053805-75-6

Upstream product

• 6436-59-5 ethyl 2-methylthiazole-4-carboxylate 

Downstream Products

• 1207472-60-3 ((R)-2-{3-[methyl-(N-methyl-(R)-pipecolyl-(S)-isoleucyl)amino]-4-methylpentyl}thiazole-4-carbonyl)(S)-phenylaniline trifluoroacetic acid salt 
• 1266208-72-3 C₃₄H₅₁N₅O₅S 
• 1266207-88-8 C₄₁H₅₅N₅O₇S 
• 1207472-57-8 methyl (4R)-4-[((R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carbonyl)amino]-5-phenylpentanoate 
• 1207472-56-7 (4R)-4-[((R)-2-{3-[(N,N-dimethylglycyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxyl)amino]-5-phenylpentanoic acid trifluoroacetic acid salt 
• 1207472-54-5 methyl (4R)-4-[((R)-2-{3-[(N,N-dimethylglycyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carbonyl)amino]-5-phenylpentanoate 
• 1207472-53-4 methyl (4R)-4-[((R)-2-{3-[(N-benzyloxycarbonyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carbonyl)amino]-5-phenylpentanoate 
• 1219930-75-2 methyl (2S,4R)-2-methyl-4-[({2-[(3R)-4-methyl-3-{methyl[(2S,3S)-3-methyl-2-({[(2R)-1-methylpiperidin-2-yl]carbonyl}amino)pentanoyl]amino}pentyl]-1,3-thiazol-4-yl}carbonyl)amino]-5-phenylpentanoate 
• 1174764-24-9 (4R)-4-[((R)-2-{3-[methyl-(N-methyl-(R)-pipecolyl-(S)-isoleucyl)-amino]-4-methyl-pentyl}-thiazole-4-carbonyl)-amino]-5-phenyl-pentanoic acid trifluoroacetic acid salt 

Relevant academic research and scientific papers

Development of a practical and scalable route for the preparation of the deacetoxytubuvaline (dTuv) fragment of pretubulysin and analogs

We present herein a novel and convenient route for the scaling-up of the dTuv fragment of pretubulysin. The newly conceived chemical path involves a practical and efficient one-step procedure for the preparation of a key thiazole intermediate, followed by high-yielding Wittig olefination/reduction steps. The optimized route, starting from the inexpensive and non-toxic l-cysteine, encompasses five synthetic steps and only two chromatographic purifications, thus displaying a dramatically increased overall yield. The versatility of the proposed approach also provides new hints for the exploration of pretubulysin derivatives bearing diverse heterocyclic portions.

Design, synthesis, and antitumor activity evaluation of pretubulysin analogs

Pretubulysin, a biosynthetic precursor of the tubulysins, shows potent biological activity in a variety of tumor cell lines. Although there are several total synthesis routes to tubulysin and pretubulysin reported, the commercialization still has been hampered due to the complexity of the structure. To find structurally simpler pretubulysin analogs, a series of 2-(3-(methylamino)propyl)thiazole-4-carboxamides are designed and synthesized, and their anticancer activities are screened using MCF-7 (breast cancer), and NCI-H157 (lung cancer) cell lines. Taxol (IC50?=?0.01?μM) and pretubulysin are used as the control. Compounds 8c (IC50?=?0.05?μM, MCF-7; 0.09?μM, NCI-H157) and 8h (IC50?=?0.01?μM, MCF-7; 0.02?μM, NCI-H157) exhibited certain antitumor activities comparable to those of Taxol. The urea analogs of pretubulysin might represent a promising scaffold for the further development of novel antitumor drugs.