133908-08-4Relevant academic research and scientific papers
First Total Synthesis and Structure-Activity Relationship of Iheyamide A, an Antitrypanosomal Linear Peptide Isolated from a Dapissp. Marine Cyanobacterium
Gerwick, William H.,Iwasaki, Arihiro,Jeelani, Ghulam,Kurisawa, Naoaki,Nozaki, Tomoyoshi,Rahmawati, Yulia,Suenaga, Kiyotake,Teranuma, Kazuya
, p. 2587 - 2593 (2021/09/28)
Iheyamide A ( 1 ) is an antitrypanosomal linear peptide isolated from aDapissp. marine cyanobacterium by our group in 2020, and based on structure-activity relationships of its natural analogues, the C-terminal pyrrolinone moiety has been identified as the phamacophore for its antiparasitic activity. Further, we isolated this pyrrolinone moiety by itself as a new natural product from the marine cyanobacterium and named it iheyanone ( 2 ). As expected, iheyanone ( 2 ) showed antitrypanosomal activity, but its potency was weaker than iheyamide A ( 1 ). To clarify more detailed structure-activity relationships, we completed a total synthesis of iheyamide A ( 1 ) along with iheyanone ( 2 ) and evaluated the antitrypanosomal activities of several synthetic intermediates. As a result, we found that the longer the peptide chain, the stronger the antitrypanosomal activity. As iheyamide A ( 1 ) showed selective toxicity againstTrypanosoma brucei rhodesiense, these findings can provide design guidelines for antitrypanosomal drugs.
Synthesis of gallinamide A analogues as potent falcipain inhibitors and antimalarials
Conroy, Trent,Guo, Jin T.,Elias, Nabiha,Cergol, Katie M.,Gut, Jiri,Legac, Jennifer,Khatoon, Lubna,Liu, Yang,McGowan, Sheena,Rosenthal, Philip J.,Hunt, Nicholas H.,Payne, Richard J.
, p. 10557 - 10563 (2015/02/19)
Analogues of the natural product gallinamide A were prepared to elucidate novel inhibitors of the falcipain cysteine proteases. Analogues exhibited potent inhibition of falcipain-2 (FP-2) and falcipain-3 (FP-3) and of the development of Plasmodium falciparum in vitro. Several compounds were equipotent to chloroquine as inhibitors of the 3D7 strain of P. falciparum and maintained potent activity against the chloroquine-resistant Dd2 parasite. These compounds serve as promising leads for the development of novel antimalarial agents.
Efficient total synthesis of dysidenin, dysidin, and barbamide
Ilardi, Elizabeth A.,Zakarian, Armen
supporting information; experimental part, p. 2260 - 2263 (2012/06/30)
The total syntheses of three trichloroleucine-derived marine natural products-dysidenin, dysidin, and barbamide-capitalized on a practical and highly diastereoselective ruthenium catalyzed radical chloroalkylation of N-acyloxazolidinones as the key step. Copyright
Total synthesis of malyngamide X and its 7′S-epi isomer
Suntornchashwej, Suchada,Suwanborirux, Khanit,Isobe, Minoru
, p. 3217 - 3226 (2007/10/03)
Stereoselective syntheses of malyngamide X (1) and its 7′(S)-epimer are described. A Lewis acid (Et2AlCl) mediated anti-aldol reaction was employed to generate the stereocenters C-7 and C-8. The route is convergent and provides a convenient acc
