10-Hydroxycamptothecin

Base Information

• Chemical Name: 10-Hydroxycamptothecin
• CAS No.: 19685-09-7
• Deprecated CAS: 104155-90-0,157405-42-0
• Molecular Formula: C20H16N2O5
• Molecular Weight: 364.357
• Hs Code.: 29349990
• European Community (EC) Number: 805-668-4
• NSC Number: 107124
• UNII: 9Z01632KRV
• DSSTox Substance ID: DTXSID00941444
• Nikkaji Number: J3.021.724A,J258.662B
• Wikidata: Q27155328
• Pharos Ligand ID: 3BK9M2WMF3S9
• Metabolomics Workbench ID: 129978
• ChEMBL ID: CHEMBL273862
• Mol file: 19685-09-7.mol

Synonyms:10-hydroxycamptothecin;10-hydroxycamptothecine

Chemical Property of 10-Hydroxycamptothecin

Chemical Property:

• Appearance/Colour: Yellow solid
• Vapor Pressure: 1.67E-28mmHg at 25°C
• Melting Point: 265-270 °C
• Refractive Index: 1.776
• Boiling Point: 820.7 °C at 760 mmHg
• PKA: 8.93±0.40(Predicted)
• Flash Point: 450.1 °C
• PSA: 101.65000
• Density: 1.6 g/cm³
• LogP: 1.78520
• Storage Temp.: -20°C Freezer
• Solubility.: ≥23.8 mg/mL in DMSO with gentle warming; insoluble in EtOH; insoluble in H2O
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 364.10592162
• Heavy Atom Count: 27
• Complexity: 774

Purity/Quality:

99% ^*data from raw suppliers

SN 38 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(C2=C(COC1=O)C(=O)N3CC4=C(C3=C2)N=C5C=CC(=CC5=C4)O)O
• Isomeric SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=C(C3=C2)N=C5C=CC(=CC5=C4)O)O
• Description: DNA topoisomerases relax supercoiled DNA during replication, transcription, recombination, repair, and chromosome condensation. The relaxation of DNA supercoiling by topoisomerase I at single-strand breaks represents a target for anticancer agents to intercalate between DNA base pairs, leading to the activation of apoptotic and cell cycle arrest pathways. (S)-10-hydroxy-Camptothecin is an inhibitor of topoisomerase I originally isolated from the Chinese tree C. acuminata. It is a member of the camptothecin family that demonstrates less toxicity than its parent compound. (S)-10-hydroxy-Camptothecin has strong anti-tumor activity against a wide range of experimental tumors including L1210 leukemia cells (IC50 = 1.15 μM). In vitro treatment of human HepG2 cells with 5-20 μM (S)-10-hydroxy-camptothecin results in cell cycle arrest at the G2/M phase.
• Uses: A Camptothecin derivative; a topoisomerase inhibitor for cancer therapy

Technology Process of 10-Hydroxycamptothecin

There total 65 articles about 10-Hydroxycamptothecin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.5%

10-hydroxycamptothecin → (S)-10-hydroxycamptothecin (19685-09-7,64439-81-2)

Guidance literature:

In 1,4-dioxane; acetonitrile; for 0.75h; UV-irradiation;

Reference yield: 82.0%

10-methoxycamptothecin (19685-10-0) → (S)-10-hydroxycamptothecin (19685-09-7,64439-81-2)

Guidance literature:

With hydrogen bromide; at 110 ℃; for 72h;

DOI:10.1002/(SICI)1521-3765(199801)4:1<67::AID-CHEM67>3.0.CO;2-F

Reference yield: 58.0%

Camptothecin 1-oxide (86639-48-7) + ethyl 2-sulfanylacetate (623-51-8) → (S)-10-hydroxycamptothecin (19685-09-7,64439-81-2) + ((S)-4-Ethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-ylsulfanyl)-acetic acid ethyl ester (86639-49-8)

Guidance literature:

With sulfuric acid; In 1,4-dioxane; for 0.5h; Irradiation;

DOI:10.1248/cpb.39.3183

upstream raw materials:

methanol

Camptothecin 1-oxide

acetic acid

1,2,6,7-tetrahydrocamptothecin

Downstream raw materials:

DB-67

9-amino-20(S)-camptothecin

7-ethyl-10-hydroxycamptothecin

10-[4-(2,3,4-tri-O-acetyl-6-O-methyl-β-D-glucuronyloxy)-3-nitrobenzyloxy]camptothecin

Refernces

• 1、 Liu, Guan-Sai,Dong, Qing-Li,Yao, Yuan-Shan,Yao, Zhu-Jun. "Expeditious total syntheses of camptothecin and 10-hydroxycamptothecin". . p. 5393 - 5396. Retrieved 2008.
• 2、 Sekhar,Anjaneyulu, Yerramilli,Acharyulu, V.R.Palle. "Synthesis of 10-hydroxycamptothecin: Evaluation of new moderators for the chemoselective reduction of camptothecin". . p. 2828 - 2834. Retrieved 2011.
• 3、 -. "Chemical semi-synthesis process of 10-hydroxycamptothecine". Paragraph 0006; 0007. . Retrieved 2016/10/10.