Sansalvamide A - CAS 227084-43-7
Catalog number: 227084-43-7
Category: Inhibitor
Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Molecular Formula:
C32H50N4O6
Molecular Weight:
586.76
COA:
Inquire
Targets:
Hsp90
Description:
Sansalvamide A binds directly to Hsp90 and modulate Hsp90's binding with client proteins.
Brife Description:
Sansalvamide A binds directly to Hsp90 and modulate Hsp90's binding with client proteins.
Purity:
>98%
Appearance:
Solid powder
Storage:
3 years -20oC powder, 6 months-80oC in solvent.
MSDS:
Inquire
Quality Standard:
In-house
Quantity:
Grams-Kilos
Melting Point:
143-145 °C
InChIKey:
YIRQWXGQCMAHIW-IRGGMKSGSA-N
InChI:
InChI=1S/C32H50N4O6/c1-18(2)14-23-28(37)33-24(17-22-12-10-9-11-13-22)29(38)35-25(15-19(3)4)32(41)42-26(16-20(5)6)30(39)36-27(21(7)8)31(40)34-23/h9-13,18-21,23-27H,14-17H2,1-8H3,(H,33,37)(H,34,40)(H,35,38)(H,36,39)/t23-,24-,25-,26-,27-/m0/s1
Canonical SMILES:
CC(C)CC1C(=O)NC(C(=O)NC(C(=O)OC(C(=O)NC(C(=O)N1)C(C)C)CC(C)C)CC(C)C)CC2=CC=CC=C2
1.Synthesis of second-generation sansalvamide A derivatives: novel templates as potential antitumor agents.
Rodriguez RA;Pan PS;Pan CM;Ravula S;Lapera S;Singh EK;Styers TJ;Brown JD;Cajica J;Parry E;Otrubova K;McAlpine SR J Org Chem. 2007 Mar 16;72(6):1980-2002. Epub 2007 Feb 22.
We report the synthesis of 34 second-generation Sansalvamide A derivatives. San A derivatives have unique anticancer properties and target multiple cancers, including colon, pancreatic, breast, prostate, and melanoma. As novel templates, the derivatives described herein explore the role of stereochemistry, amide bond geometry, transannular hydrogen bonding, and polarity on antitumor potency. Testing the chemotherapeutic activity of these derivatives against multiple cancer cell lines will provide clear structural motifs and identify conformational space that is important for cytotoxicity. The 34 compounds presented are divided into six series, where five series involve the insertion of D-amino acids in conjunction with four structural features at each of the five positions of the macrocycle. The sixth series involves comparison between all L- and all D-amino acid derivatives with N-methyls placed at each position around the macrocyclic core. The four structural features explored in conjunction with D-amino acids include N-methyl amino acids, aromatic amino acids, polar amino acids, and hydrophobic alkyl amino acids.
2.Consecutive isocyanide-based multicomponent reactions: synthesis of cyclic pentadepsipeptoids.
Barreto Ade F;Vercillo OE;Wessjohann LA;Andrade CK Beilstein J Org Chem. 2014 May 5;10:1017-22. doi: 10.3762/bjoc.10.101. eCollection 2014.
The synthesis of six cyclic depsipeptoids inspired by the natural depsipeptide sansalvamide A is described. An efficient and fast synthetic strategy was developed using a combination of consecutive isocyanide-based multicomponent reactions (Ugi and Passerini reactions). This methodology can be used to access a variety of cyclic oligodepsipeptoids.
3.Synthesis of sansalvamide A peptidomimetics: triazole, oxazole, thiazole, and pseudoproline containing compounds.
Davis MR;Singh EK;Wahyudi H;Alexander LD;Kunicki JB;Nazarova LA;Fairweather KA;Giltrap AM;Jolliffe KA;McAlpine SR Tetrahedron. 2012 Jan 28;68(4):1029-1051.
Peptidomimetic-based macrocycles typically have improved pharmacokinetic properties over those observed with peptide analogs. Described are the syntheses of 13 peptidomimetic derivatives that are based on active Sansalvamide A structures, where these analogs incorporate heterocycles (triazoles, oxazoles, thiazoles, or pseudoprolines) along the macrocyclic backbone. The syntheses of these derivatives employ several approaches that can be applied to convert a macrocyclic peptide into its peptidomimetic counterpart. These approaches include peptide modifications to generate the alkyne and azide for click chemistry, a serine conversion into an oxazole, a Hantzsch reaction to generate the thiazole, and protected threonine to generate the pseudoproline derivatives. Furthermore, we show that two different peptidomimetic moieties, triazoles and thiazoles, can be incorporated into the macrocyclic backbone without reducing cytotoxicity: triazole and thiazole.
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