482-22-4

Usage

Uses

Used in Pharmaceutical Industry:
Cryptopleurine is used as an anti-cancer agent for its therapeutic potentials against various types of cancer. It has shown promise in targeting and inhibiting cancer cell growth, making it a valuable compound in the development of novel cancer treatments.
Used in Cancer Research:
In the field of cancer research, cryptopleurine is utilized as a key compound for studying the mechanisms of cancer cell growth and proliferation. Its unique structure and properties allow researchers to investigate new approaches to combat cancer and develop more effective therapies.
Used in Drug Development:
Cryptopleurine is also used in the development of new drugs and drug delivery systems, as its anti-cancer properties can be harnessed to create more targeted and effective treatments. By incorporating cryptopleurine into drug formulations, researchers aim to improve the efficacy of cancer therapies and reduce side effects associated with traditional chemotherapy.

InChI:InChI=1/C24H27NO3/c1-26-16-7-8-17-19(11-16)21-13-24(28-3)23(27-2)12-20(21)18-10-15-6-4-5-9-25(15)14-22(17)18/h7-8,11-13,15H,4-6,9-10,14H2,1-3H3/t15-/m1/s1

Upstream product

• 162869-95-6 11,12,13,14,14a,15-Hexahydro-2,3,6-trimethoxy-9H-phenanthro<9,10-b>quinolizin-9-one 
• 50-00-0 formaldehyd 
• 697234-86-9 (R)-2-((2,3,6-trimethoxyphenanthren-10-yl)methyl)piperidine 
• 697234-90-5 (S)-[1-[(3,6,7-trimethoxyphenanthren-9-yl)methyl]but-2-enyl]carbamic acid benzyl ester 
• 1027077-43-5 1-(2-Bromo-4,5-dimethoxy-phenyl)-2-(R)-piperidin-2-yl-ethanol 
• 906534-14-3 (9R,9aR)-3,6,7-Trimethoxy-9,10,11,12,13,14-hexahydro-9aH-13a-aza-benzo[b]triphenylen-9-ol 
• 87302-60-1 (15S)-15-hydroxy-2,3,6-trimethoxyphenanthro<9,10-b>quinolizidine 
• 1217508-57-0 C₂₄H₂₅NO₄ 
• 4693-91-8 4-methoxyphenyl-acetic chloride 
• 167933-98-4 (2R)-2-<(3,4-Dimethoxybenzoyl)methyl>-N-<(4-methoxyphenyl)acetyl>piperidine 
• 1414774-99-4 (R)-3-(3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)-7,8,9,9a-tetrahydro-1H-quinolizin-4(6H)-one 
• 28697-17-8 N-BOC-D-pipecolic acid 
• 203056-15-9 tert-butyl (2R)-2-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate 
• 1588418-49-8 C₂₅H₂₇NO₄ 

Relevant academic research and scientific papers

Total Synthesis of Cryptopleurine and Its Analogues

Total synthesis of phenanthroquinolizidine alkaloid cryptopleurine was achieved in 8 steps from commercially available 2-pyridinecarboxaldehyde and the epoxide derived from methyleugenol. The key intermediate vinyl triflate enables the divergent synthesis of cryptopleurine derivatives by late-stage installation of various substituents on the C-ring.

Synthesis of (-)-cryptopleurine by combining gold(I) catalysis with a free radical cyclization

(R)-(-)-Cryptopleurine, a highly cytotoxic alkaloid found in Cryptocarya and Boehmeria species, was synthesized in high optical purity using a gold(I)-NHC catalyzed cyclization of an unsymmetrical phenanthrene precursor combined with a free radical cyclization to achieve closure of the C-ring.

Antofine and cryptopleurine derivatives as anticancer agents

The present invention provides compounds of Formula (I-IV): compositions containing the same, and methods of use thereof such as for the treatment of cancer.

Synthesis and biological evaluation of (-)-6-O-desmethylcryptopleurine and analogs

(-)-Cryptopleurine 1 is one of the most potent anti-proliferative member of the phenanthroquinolizidine class of alkaloids. We report here the synthesis of (-)-6-O-desmethylcryptopleurine (-)-2 and (-)-6-O-desmethyl-(15R)-hydroxycryptopleurine (-)-4 in th

Collective asymmetric synthesis of (-)-Antofine, (-)-cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine with tert- butanesulfinamide as a chiral auxiliary

A collective asymmetric synthesis of phenanthroindolizidine and phenanthroquinolizidine alkaloids (-)-antofine, (-)-cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine was achieved by means of a reaction sequence involving efficient generation of chiral homoallylic amine intermediates by asymmetric allylation of the corresponding tert-butanesulfinyl imine. From these intermediates, the pyrrolidine and piperidine rings were constructed by means of an intramolecular SN2 substitution reaction and a ring-closing metathesis reaction, respectively. The unusual C5-methoxy-substituted phenanthrene moiety of (-)-tylocrebrine was generated by means of an InCl3-catalyzed cycloisomerization reaction of an o-propargylbiaryl compound.

Total synthesis of (+)-antofine and (-)-cryptopleurine

The tylophorine alkaloid anticancer compounds antofine and cryptopleurine have been synthesized in optically active form. Both syntheses use optically pure α-amino acids as the starting materials, require only seven steps from known 2-ethynylpyrrolidine or 2-ethynylpiperidine derivatives, and are free of protecting groups. The key steps include an alkyne hydration and a chromium-carbene-complex-based net [5 + 5]-cycloaddition step. The alkyne hydration was accompanied by racemization of the β-amino ketone product under most of the conditions examined, and minimization of this side-reaction was achieved through careful pH control and choice of metal additive. The final ring closure involved a Bischler-Napieralski reaction using a carbamate (antofine) or urea (cryptopleurine) precursor. Single enantiomers of the tylophorine alkaloids antofine and cryptopleurine have been prepared by using a short synthesis that involves regioselective alkyne hydration of a chiral propargylic amide, Fischer carbene complex mediated net [5+5] cycloaddition, and urea-based Friedel-Crafts acylation as key steps. Copyright

Enantioselective synthesis of cryptopleurine and boehmeriasin A via organocatalytic intramolecular aza-Michael addition

The enantioselective synthesis of phenanthroquinolizidine alkaloids cryptopleurine and boehmeriasin A was achieved in eight steps from commercial available Cbz-protected 2-piperidinone in 22% and 20% overall yield, respectively. The key steps of this route are intramolecular enantioselective aza-Michael addition, intramolecular aldol addition, and oxidative coupling.

Antitumor agents. 274. A new synthetic strategy for E-ring SAR study of antofine and cryptopleurine analogues

Chemical equation presented A new versatile synthetic methodology for the synthesis of enantiomerically pure natural phenanthroindolizidines and phenanthroquinolizidines has been established and described. Natural products R-antofine and R-cryptopleurine, as well as a novel E-ring expanded analogue 13c (E7), 12-oxo-S-antofine (17), and 12N-methyl-12-aza-S-antofine (18) were synthesized with the new method. This strategy will greatly facilitate future SAR studies on the natural alkaloids with E-ring variations.

Highly efficient synthesis of phenanthroquinolizidine alkaloids via Parham-type cycliacylation

A concise and efficient route involving Parham-type cycliacylation as the key step has been used to synthesize phenanthroquinolizidine alkaloids 1a-c and 2a-c. Among the products, 1b-(S), 1b-(R), 2a-(14aS,15S), 2a-(14aR,15R), and 2b were synthesized for the first time.

Asymmetric synthesis of (R)-antofine and (R)-cryptopleurine via proline-catalyzed sequential α-aminoxylation and Horner-Wadsworth-Emmons olefination of aldehyde

Naturally occurring phenanthroindolizidine alkaloids (R)-antofine and phenanthroquinolizidine alkaloids (R)-cryptopleurine have been synthesized in high optical purity via proline-catalyzed sequential α-aminoxylation and Horner-Wadsworth-Emmons olefinatio