148441-26-3

Basic information

• Product Name: 5-N-acetylardeemin
• Synonyms: 5-N-acetylardeemin
• CAS NO: 148441-26-3
• Molecular Formula: C28H28N4O3
• Molecular Weight: 468.554
• Mol File: 148441-26-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 701.4°Cat760mmHg
• Flash Point: 378°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 1.6E-19mmHg at 25°C
• Refractive Index: 1.698
• CAS DataBase Reference: 5-N-acetylardeemin(CAS DataBase Reference)
• NIST Chemistry Reference: 5-N-acetylardeemin(148441-26-3)
• EPA Substance Registry System: 5-N-acetylardeemin(148441-26-3)

Safety Data

• Hazardous Substances Data: 148441-26-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C28H28N4O3/c1-6-27(4,5)28-15-22-23-29-20-13-9-7-11-18(20)25(35)30(23)16(2)24(34)32(22)26(28)31(17(3)33)21-14-10-8-12-19(21)28/h6-14,16,22,26H,1,15H2,2-5H3/t16-,22+,26+,28-/m1/s1

Upstream product

• 1064604-21-2 methyl (2S,3aR,8aR)-[3a-bromo-(1,2,3,3a,8,8a)-hexahydropyrrolo[2,3-b]indole-1,8-di-tertbutoxycarbonyl]-2-carboxylate 
• 1352521-58-4 C₂₇H₂₈N₄O₂ 
• 1352521-56-2 C₂₇H₂₈N₆O₃ 
• 1352521-54-0 C₂₀H₂₅N₃O₂ 
• 1352521-53-9 C₃₆H₃₉N₃O₅ 
• 1352521-51-7 C₃₅H₃₇N₃O₅ 
• 159333-20-7 (2S,3aR,8aR)-methyl 3a-(2-methylbut-3-en-2-yl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate 
• 4299-70-1 L-tryptophan methyl ester 
• 159333-18-3 (2S,3aR,8aR)-1,8-ditert-butyl 2-methyl 3a-(2-methylbut-3-en-2-yl)-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate 
• 159333-22-9 (2S,3aR,8aR)-3a-(1,1-Dimethyl-allyl)-2-((R)-1-methoxycarbonyl-ethylcarbamoyl)-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,8-dicarboxylic acid di-tert-butyl ester 
• 159333-24-1 (3R,5aS,10bR,11aS)-2-(2-Azido-benzoyl)-10b-(1,1-dimethyl-allyl)-3-methyl-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione 
• 159333-19-4 (2S,3aR,8aR)-3a-(1,1-Dimethyl-allyl)-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 1,8-di-tert-butyl ester 
• 258883-28-2 (2S,3aR,8aR)-3a-(1,1-Dimethyl-allyl)-2-fluorocarbonyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,8-dicarboxylic acid di-tert-butyl ester 
• 258883-30-6 (R)-2-{[(2S,3aR,8aR)-3a-(1,1-Dimethyl-allyl)-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl]-amino}-propionic acid methyl ester 

Relevant articles and documents

Stereoselective total syntheses of amauromine and 5-N-acetylardeemin. A concise route to the family of 'reverse-prenylated' hexahydropyrroloindole alkaloids

-

Total syntheses of (-)-fructigenine A and (-)-5-N-acetylardeemin

(Chemical Equation Presented) The first total synthesis of (-)-fructigenine A and a novel approach to (-)-5-N-acetylardeemin through a common imine intermediate (+)-3 are described. The key steps include highly enantioselective preparation of (+)-3 via domino olefination/isomerization/Claisen rearrangement (OIC) of 5, reductive cyclization (RC), and regioselective oxidation of (-)-4 and a novel assembly of the pyrazino ring of these alkaloids via Ugi three-component reaction/cyclization of (+)-3 with the corresponding amino acid and isonitrile.

ANALOGUES OF N-ACETYLARDEEMIN, METHOD OF PREPARATION AND USES THEREOF

The present invention provides a compound having the structure: wherein R1 R6 and R7 are independently hydrogen, OH, NH2, SH, halogen, C1-C9 linear or branched chain alkyl, alkylmercapto, alkylamino, dialkylamino, alkoxy, phenyl, etc.; wherein R0 and R2 are independently hydrogen, OH, linear or branched chain alkyl, -CR3R3-CH(O)CH2, -CR3R3-CH2CH3, -CR3R3-CH2CH2OH, -CR3R3-CH(OH)R4 or -CR3R3-CH=CHR4; wherein R3 and R4 are independently hydrogen, halogen, C1-C9 linear or branched chain alkyl, phenyl, etc.; wherein R5 is hydrogen, C1-C9 linear or branched chain alkyl, phenyl, etc.; and wherein R8 is hydrogen, C1-C9 linear or branched chain acyl, benzoyl, etc.; with the proviso that (a) when R2 is -CR3R3-CH(O)CH2, -CR3R3-CH2CH3, -CR3R3-CH2CH2OH, -CR3R3-CH(OH)R4 or -CR3R3-CH=CHR4, then R2 is hydrogen; (b) when R0 is -CR3R3-CH(O)CH2, -CR3R3-CH2CH3, -CR3R3-CH2CH2OH, -CR3R3-CH(OH)R4 or -CR3R3-CH=CHR4, then R2 is OH; and (c) when (i) R0 or R2 is -CR3R3-CH=CHR4, (ii) R3 and R5 are CH3 and (iii) R4 is hydrogen, then R1, R6 and R7 are not all hydrogen. Also provided are related compounds and compositions, and methods of inhibiting the growth of multidrug resistant cells by means of MDR reversal, collateral sensitivity and quantitative synergism.