19685-10-0

Usage

Uses

Used in Oncology:
9-Methoxycamptothecin is used as an anticancer agent for the treatment of various types of cancers. As a derivative of Camptothecin, a potent anti-cancer agent, it contributes to the management of hyperproliferative diseases by targeting and inhibiting essential cellular processes in cancer cells.
Used in Pharmaceutical Industry:
9-Methoxycamptothecin is utilized as a key component in the development of cancer therapeutics. Its role in this industry is crucial due to its potential to treat a range of cancer types and its contribution to the advancement of cancer treatment options.

References

Govindachari, Viswanathan., Phytochem., 11, 3529 (1972) Govindachari, Viswanathan.,Ind. J. Chem., 10,453 (1972)

InChI:InChI=1/C21H18N2O5/c1-3-21(26)15-8-17-18-12(6-11-7-13(27-2)4-5-16(11)22-18)9-23(17)19(24)14(15)10-28-20(21)25/h4-8,26H,3,9-10H2,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 19685-09-7 (S)-10-hydroxycamptothecin 
• 67-56-1 methanol 
• 86639-48-7 Camptothecin 1-oxide 
• 10349-38-9 p-methoxyphenylisonitrile 
• 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 
• 74-88-4 methyl iodide 
• 1088402-95-2 10-methoxy-21-hydroxycamptothecin 
• 1353579-41-5 (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(3-(hydroxymethyl)-2-methoxypyridin-4-yl)propan-1-ol 
• 1353579-43-7 4-((S)-1-(benzyloxy)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-propyl)-3-((benzyloxy)methyl)-2-methoxypyridine 
• 1353579-45-9 (2R,3S)-3-(benzyloxy)-3-(3-((benzyloxy)methyl)-2-methoxypyridin-4-yl)pentane-1,2-diol 
• 1201830-88-7 (S)-2-(benzyloxy)-2-(3-((benzyloxy)methyl)-2-methoxypyridin-4-yl)butanal 
• 1201830-89-8 (S)-2-(benzyloxy)-2-(3-((benzyloxy)methyl)-2-methoxypyridin-4-yl)butanoic acid 
• 16498-81-0 2-methoxynicotinic acid 

Downstream Products

• 19685-09-7 (S)-10-hydroxycamptothecin 
• 58546-28-4 12-amino-20(S)-camptothecin 
• 1394865-84-9 10-methoxycamptothecin-20-O-2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid ester 
• 119413-54-6 Topotecan hydrochloride 

Related news

The quinoline alkaloids camptothecin and 9-methoxycamptothecin (cas 19685-10-0) from tissue cultures and mature trees of Nothapodytes foetida09/02/2019

Tissue cultures of the indigenous tree Nothapodytes foetida were established from immature embryos on Murashige and Skoog's agar medium supplemented with different auxins and cytokinins. The embryos developed unorganized callus tissues in medium containing BA + 2,4-D. BA + NAA medium promot...detailed

Relevant academic research and scientific papers

A new strategy to improve the metabolic stability of lactone: Discovery of (20 S,21 S)-21-fluorocamptothecins as novel, hydrolytically stable topoisomerase i inhibitors

Lactone is a common structural motif in biologically active natural products. However, the metabolic instability of lactone significantly reduces their in vivo potency. In the present investigation, a new strategy to improve the metabolic stability of lactone was provided by the design of α-fluoro ether as a novel bioisostere of lactone. The effectiveness of the α-fluoro ether/lactone replacement was validated by the discovery of (20S,21S)-21-fluorocamptothecins as hydrolytically stable topoisomerase I inhibitors. A highly potent camptothecin derivative, 8l, was successfully identified, which showed excellent in vitro and in vivo antitumor activities and represents a promising lead for the discovery of novel antitumor agents. Interestingly, this study also provided a new structure-activity relationship for the C21-carbonyl group of camptothecin, which has been regarded as an essential pharmacophore. Our results revealed that the conserved C21-carbonyl group can be replaced by a fluorine substituent. α-Fluoro ether may have general application in improving the metabolic stability of lactone.

Selective phenolic acylation of 10-hydroxycamptothecin using poly (ethylene glycol) carboxylic acid

Selective acylation of the phenolic hydroxyl group of 10-hydroxycamptothecin has been accomplished using phenyl dichlorophosphate. Additional modification of the 10-OH as an ether permits a 20-acyl derivative to be synthesized. This result along with data from a 6-hydroxyquinoline model strongly suggests that powerful intermolecular hydrogen bonding exists in the parent molecule.

CONJUGATES OF A CELL-BINDING MOLECULE WITH CAMPTOTHECIN ANALOGS

Provided are conjugates of camptothecin analogs with a cell-binding molecule of formula (I), wherein R1, R2, R3, R4, R5, X, L, n, m, T and ----- are defined herein. It also provides methods of making the conjugates of camptothecin analogs to a cell-binding agent, as well as methods of using the conjugates in targeted treatment of cancer, infection, and immunological disorders.

Water-soluble anti-tumor compounds

The invention relates to a water-soluble antitumor compound represented by the formula (I), and further relates to a preparation method of the compound and an application of the compound in preparation of antitumor drugs. Stable prodrug with a good water

Visible-Light-Induced Radical Cascade Cyclization: Synthesis of (20S)-Camptothecin, SN-38 and Irinotecan

(20S)-Camptothecin, irinotecan and SN-38 were successfully synthesized by a photocatalyzed radical cascade cyclization from an N-propargyl iodopyridinone and an arylisonitrile under visible light with a ruthenium catalyst. This synthetic method provided a useful entry into composing camptothecin family of antitumor agents in good yields under mild reaction conditions without the use of heavy metal reagents.

Synthesis and anticancer evaluation of novel 10-methoxycamptothecin derivatives

As part of our continuing search for potential anticancer drug candidates, we have synthesized four 10-methoxycamptothecin derivatives. The compounds were synthesized by facile procedures and characterized by 1H NMR, 13C NMR and mass spectra study. The synthesized compounds were examined for their cytotoxic effect on a panel of five human cancer cell lines. Three out of five compounds were found to exhibit moderate anticarcinogenic activities in all cell lines. The result of the present investigation encourage us to develop more other related compounds and to screen them for a wide range of biological activity.

Short protecting group-free syntheses of camptothecin and 10-hydroxycamptothecin using cascade methodologies

A convergent protecting group-free total synthesis route of camptothecin and 10-hydroxycamptothecin has been developed in this work. Cascade oxidation of 3-(hydroxymethyl)furan-2(5 H)-one and in situ intermolecular oxa Diels-Alder reaction with vinyl ether was developed and applied to construct the E-ring, and TMSCl-promoted cascade closure of the D-ring delivered the whole skeleton of the alkaloids in the total synthesis. The new short syntheses were advantageous with regard to step economy, low cost, easily available starting materials and reagents, and convenient operations.

Synthesis of 9-allyl-10-hydroxycamptothecin via Suzuki reaction

A facile and eco-friendly approach for synthesizing 9-allyl-10- hydroxycamptothecin (2), a key intermediate for the preparation of camptothecin analogs, is described. The product was obtained in good yield and high purity (≥99% HPLC) under mild Suzuki reaction condition.

Total synthesis of camptothecin and SN-38

A new practical and concise total synthesis of enantiopure camptothecin and SN-38 (14% overall yield, 99.9% ee and 99.9% purity) was described, starting from inexpensive and readily available materials. The development of column chromatography-free purification was achieved in all steps, which offers an economic industrial process to the camptothecin-family alkaloids.

Synthesis of new cytotoxic E-ring modified camptothecins

In an effort to decrease the toxicity and improve the stability of the E-ring of camptothecin, new analogues with an 'inverted' lactone ring were designed and synthesized. The compounds retained a good cytotoxic activity on human non-small lung cancer cel