66212-45-1Relevant articles and documents
Chondropsins A and B: Novel tumor cell growth-inhibitory macrolide lactams from the marine sponge Chondropsis sp
Cantrell,Gustafson,Cecere,Pannell,Boyd
, p. 8825 - 8829 (2000)
Antiproliferative bioassay-guided fractionation of an aqueous extract of the marine sponge Chondropsis sp. provided two novel macrolides, chondropsins A (1) and B (2). The structures were elucidated by a combination of spectroscopic analysis and chemical modification. HMBC, TOCSY, NOESY, and HSQC-TOCSY experiments were particularly useful for the structural assignments of these polyketide-derived metabolites. The chondropsins define an unprecedented class of polyunsaturated, polyhydroxylated, 35-membered macrocycles which incorporate both lactone and lactam functionalities. An additional unique feature of these compounds is a complex, amide-linked, polyketide side chain. Testing of chondropsin A (1) in the NCI 60-cell screen revealed a mean-graph profile that did not correlate significantly with the profile of any compound class represented in the NCI standard agents database. The chondropsins therefore represent an interesting new lead for cancer therapeutics research.
Synthesis of phenolic components of Grains of Paradise
Hattori, Hiroyuki,Mitsunaga,Clive, Derrick L.J.
supporting information, p. 1989 - 1991 (2019/07/03)
Two vanilloids, (5E)-8-(4-hydroxy-3-methoxyphenyl)oct-5-en-4-one (1) and 4-[3-hydroxydecyl]-2-methoxyphenol (2), isolated from the dried seeds of Grains of Paradise (Aframomum melegueta), were synthesized; the latter compound was made as the S-enantiomer and the material derived from the seeds was found to be a 1:1.7 mixture of the R and S isomers. The synthetic route used should allow the preparation of analogs having extended alkyl chains and consequently different lipophilicity, and 3, a homolog of 2, was also prepared.
Application of the DP4 Probability Method to Flexible Cyclic Peptides with Multiple Independent Stereocenters: The True Structure of Cyclocinamide A
Cooper, Jason K.,Li, Kelin,Aubé, Jeffrey,Coppage, David A.,Konopelski, Joseph P.
supporting information, p. 4314 - 4317 (2018/07/29)
A DP4 protocol has been successfully utilized to establish the true structure of the natural product cyclocinamide A, a flexible cyclic peptide with four isolated stereocenters. Benchmarking the necessary level of theory required to successfully predict t
Total synthesis and stereochemical assignment of nostosin B
Wang, Xiaoji,Feng, Junmin,Xu, Zhengshuang,Ye, Tao,Meng, Yi,Zhang, Zhiyu
, (2017/04/06)
Nostosins A and B were isolated from a hydrophilic extract of Nostoc sp. strain from Iran, which exhibits excellent trypsin inhibitory activity. Nostosin A was the most potent natural tripeptide aldehyde as trypsin inhibitor up to now. Both R- and S-2-hydroxy-4-(4-hydroxy-phenyl)butanoic acid (Hhpba) were prepared and incorporated into the total synthesis of nostosin B, respectively. Careful comparison of the NMR spectra and optical rotation data of synthetic nostosin B (1a and 1b) with the natural product led to the unambiguous identification of the R-configuration of the Hhpba fragment, which was further confirmed by co-injection with the authentic sample on HPLC using both reversed phase column and the chiral AD-RH column.
