110351-92-3

Usage

Uses

Used in Pharmaceutical Industry:
20R-Camptothecin is used as a cytotoxic antitumor agent for its ability to inhibit the reassociation of DNA after cleavage by topoisomerase I. This mechanism of action makes it a promising candidate for the development of anticancer drugs, particularly for the treatment of various solid malignancies.
Used in Cancer Research:
20R-Camptothecin is utilized as a key compound in cancer research to study the mechanisms of topoisomerase I inhibition and its implications in cancer cell death. This research helps in the development of novel therapeutic strategies and the identification of potential drug targets for cancer treatment.
Used in Drug Development:
20R-Camptothecin serves as a lead compound in the development of new anticancer drugs. Its unique mechanism of action and potent antitumor activity have inspired the synthesis of various camptothecin analogs and derivatives, which aim to improve the drug's efficacy, selectivity, and pharmacokinetic properties.

InChI:InChI=1/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m1/s1

Upstream product

• 529-23-7 o-aminobenzaldehyde 
• 110351-91-2 5'(R)-1,5-dioxo-5'-ethyl-5'-hydroxy-2'H,5'H,6'H-6'-oxopyrano<3',4'-f>Δ^6,8-tetrahydroindolizine 
• 1197040-29-1 phenyl isocyanate 
• 174092-80-9 (S)-4-ethyl-4-hydroxy-6-iodo-7-(prop-2-yn-1-yl)-1,7-dihydro-3H-pyrano[3,4-c]pyridino-3,8(4H)-dione 
• 841276-70-8 4-ethyl-1,12-dihydro-14H-pyrano[3',4':6,7indolizino[1,2-b]]quinolin-14-one 
• 26717-67-9 dimethyl ethylmalonate 
• 173442-34-7 (S)-4-ethyl-4-hydroxy-6-iodo-3-oxo-1H-pyrano[3,4-c]-8-pyridone 
• 57876-69-4 2-chloro-3-methyl-quinoline 
• 110351-90-1 (4'R)-4'-ethyl-1',4',7',8'-tetrahydro-4'-hydroxy-3'H,10'H-spiro[1,3-dioxolane-2,6'-pyrano[3,4-f]indolizine]-3',10'-dione 
• 694452-80-7 ethyl 2-(2-benzyl-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-3-yl)acetate 
• 103-84-4 Acetanilid 
• 73568-25-9 2-chloro-3-quinoline carboxaldehyde 
• 80231-40-9 2-iodo-3-quinolinecarboxaldehyde 

Relevant academic research and scientific papers

Synthesis of indolizinoquinolinones through three- and four-component domino Knoevenagel / hetero-Diels–Alder reactions: novel access to (+)-camptothecin

[Figure not available: see fulltext.] The fused heterocyclic indolizinoquinolinone system is a key structural feature of several highly bioactive alkaloids, including camptothecin. Camptothecin has been efficiently obtained by a three- or four-component domino Knoevenagel / hetero-Diels–Alder reaction of aldehyde, Meldrum's acid, and enol ether in the presence or absence of alcohol, followed by reductive cleavage of the amine protecting group. The obtained products were further transformed along several different routes leading to camptothecin.

Photo-triggerable hydrogel-nanoparticle hybrid scaffolds for remotely controlled drug delivery

Remotely-triggerable drug delivery systems enable the user to adjust dosing regimens on-demand based on a patient's physiological response and clinical needs. However, currently reported systems are limited by the non-specific leakage of drugs in the absence of triggering and the lack of repeatability over multiple cycles of release. To this end, we have designed a unique hydrogel-nanoparticle hybrid scaffold that provides a chemically-defined, remotely-triggerable and on-demand release of small molecule drugs. Our hybrid platform consists of three distinct components: (1) a photo-triggerable chemical compound, which serves to release a covalently-bound drug upon photo-irradiation, (2) a nanoparticle, which serves to covalently bind the photo-triggerable compound, and (3) a polymeric hydrogel, which serves to hold the drug-conjugated nanoparticle. Upon photo-irradiation, the activation of the photo-triggerable compound is designed to initiate a series of intramolecular chemical rearrangements, which would cleave the covalently-bound drug and release it from the hydrogel. The combination of these distinct components in a single scaffold proved to be an effective drug delivery system, as demonstrated by the delivery of a model drug to a malignant cancer line. Our hybrid scaffold can be easily tuned for practically any biological application of interest, thus offering immense potential for clinical therapies.

Highly efficient and mild cascade reactions triggered by bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate and a concise total synthesis of camptothecin

A mild and efficient cascade methodology is reported to construct variously substituted indolizino[1,2-b]quinolin-9(11H)-ones. Efficiently triggered by bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate under mild conditions, this cascade achieved significant enhancements in chemical yields. Utilizing this highly efficient domino reaction followed by a Sharpless dihydroxylation, an eight-step total synthesis of camptothecln was accomplished from a known pyridine derivative in direct fashion with an overall yield of 47% and 95% ee.

Practical total synthesis of (+)-Camptothecin: The full story

The evolution of our strategy for the synthesis of (+)-Camptothecin and related substances is presented in detail.

Totalsynthese von (+)-Camptothecin

Keywords: Alkaloide; Asymmetrische Synthesen; Camptothecin; Naturstoffe

Kaskaden-Radikalreaktionen von Isocyaniden: eine zweite Generation der Synthese von (20S)-Camtothecin, Topotecan, Irinotecan und G1-147211C

Keywords: Camptothecin; Isocyanide; Kaskadenreaktionen; Radikale

Plant antitumor agents. 28. Resolution of a key tricyclic synthon, 5'(RS)-1,5-dioxo-5'-ethyl-5'-hydroxy-2'H,5'H,6'H,H-6'-oxopyrano[3',4' f]Δ6,8-tetrahydroindolizine: Total synthesis and antitumor activity of 20(S)- and 20(R)-camptothecin

The resolution of the tricyclic ketone (3a + 3b) by the separation of diastereomeric adducts 4a and 4c of the precursor ketal 5 is described. The regenerated enantiomers 3a and 3b of 100% optical purity represent the key intermediates from which 20(R)-camptothecin (1a) and 20(S)-camptothecin (1b), respectively, have been prepared. The 20R analogue 1a was 10-100 times less active than the natural 20(S)-camptothecin (1b) in 9KB and 9PS cytotoxicity assays and almost inactive in in vivo L-1210 leukemia tests as compared to the highly potent and active natural compound 1b.