58957-91-8

Basic information

• Product Name: (7R-cis)-9-Acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosy l)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-5,12-naphthacenedione
• Synonyms: (7R-cis)-9-Acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosy l)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-5,12-naphthacenedione
• CAS NO: 58957-91-8
• Molecular Formula: C26H27 N O9
• Molecular Weight: 497.49
• Mol File: 58957-91-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 725.4°C at 760 mmHg
• Flash Point: 392.5°C
• Appearance: /
• Density: 1.56g/cm³
• Vapor Pressure: 4.34E-22mmHg at 25°C
• Refractive Index: 1.705
• PKA: 7.79±0.60(Predicted)
• CAS DataBase Reference: (7R-cis)-9-Acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosy l)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-5,12-naphthacenedione(CAS DataBase Reference)
• NIST Chemistry Reference: (7R-cis)-9-Acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosy l)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-5,12-naphthacenedione(58957-91-8)
• EPA Substance Registry System: (7R-cis)-9-Acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosy l)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-5,12-naphthacenedione(58957-91-8)

Safety Data

• Hazardous Substances Data: 58957-91-8(Hazardous Substances Data)

Usage

General Description

(7R-cis)-9-Acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-5,12-naphthacenedione is a chemical compound that belongs to the anthracycline class of anticancer drugs. It is commonly known as daunorubicin and is used in chemotherapy to treat various types of cancer, including leukemia, lymphoma, and solid tumors. Daunorubicin works by interfering with the replication of DNA within cancer cells, ultimately leading to their destruction. It is administered intravenously and has a number of potential side effects, including bone marrow suppression, nausea, and hair loss.

InChI:InChI=1/C26H27NO9/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3/t10-,15-,16+,17-,21+,26+/m0/s1

Upstream product

• 60660-74-4 (+)-N-Trifluoroacetyl-4-demethoxydaunorubicin 
• 63700-25-4 1-chloro-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxohexopyranose 
• 63700-24-3 2,3,6-trideoxy-4-O-(p-nitrobenzoyl)-3-(trifluoroacetamido)-α-L-lyxo-hexopyranosyl p-nitrobenzoate 
• 82343-11-1 4-Nitro-benzoic acid (2S,3R,4S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester 
• 60660-75-5 (7S,9S)-idarubicinone 
• 128572-89-4 4-Nitro-benzoic acid (2S,3R,4S)-6-chloro-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester 
• 62414-07-7 N-[(2S,3R,4S,6R)-6-((1S,3S)-3-Acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl]-2,2,2-trifluoro-acetamide 
• 82343-11-1 (-)-4'-O-p-Nitrobenzoyl-N-trifluoroacetyl-4-demethoxydaunorubicin 
• 60733-79-1 3'-N-trifluoroacetyl-4-demethoxy-7,9-bisepidaunomycin 
• 1403872-37-6 4-demethoxy-3'-N₃-daunorubicin 
• 1403872-35-4 C₂₇H₂₄F₃N₃O₁₂S 
• 1403987-61-0 4-demethyl-3'-N₃-daunorubicine 
• 874384-80-2 7-(3-azido-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)daunorubicinone 
• 23541-50-6 daunomycin hydrochloride 

Downstream Products

• 57852-57-0 idarubicin hydrochloride 

Relevant articles and documents

Method of producing 4-demethoxydaunorubicin

The present invention relates to a method for the synthesis of 4-demethoxydaunorubicin (idarubicin) having the chemical structure of formula (I), which involves the demethylation of 3'-Prot-daunorubicin in the presence of a soft Lewis acid. The method of the present invention does not comprise cleavage of the glycosidic linkage at carbon C7, thus resulting in a faster synthesis cycle and an improved yield of the final product.

Anti-Claudin 3 Monoclonal Antibody and Treatment and Diagnosis of Cancer Using the Same

Monoclonal antibodies that bind specifically to Claudin 3 expressed on cell surface are provided. The antibodies of the present invention are useful for diagnosis of cancers that have enhanced expression of Claudin 3, such as ovarian cancer, prostate cancer, breast cancer, uterine cancer, liver cancer, lung cancer, pancreatic cancer, stomach cancer, bladder cancer, and colon cancer. The present invention provides monoclonal antibodies showing cytotoxic effects against cells of these cancers. Methods for inducing cell injury in Claudin 3-expressing cells and methods for suppressing proliferation of Claudin 3-expressing cells by contacting Claudin 3-expressing cells with a Claudin 3-binding antibody are disclosed. The present application also discloses methods for diagnosis or treatment of cancers.

TARGETED DRUG DELIVERY USING SULFONAMIDE DERIVATIVES

The present invention relates to Glutathione S-transferase (GST)/Reduced Glutathione (GSH) as a means for the in-vivo release of a drug that has been conjugated to specific electrophilic moieties via a sulfonamide bond. The drug may be an anticancer agent (or one with other therapeutic properties) carrying a free —NH— which has been derivatized by the attachment of an electrophile containing a moiety, such as p-CN— or p-NO 2-pyridinylsulfonyl groups, or p-NO 2- or 2,4 dinitrophenylsulfonyl groups, or suitable derivatives thereof, to make a prodrug. Optionally, the sulfonamide moiety may have attached to it a targeting molecule. The present invention also provides Glutathione S-transferase (GST)/Reduced Gluthathione (GSH) as a means for the release of a protected amino derivative that has been conjugated to specific electrophilic moieties via a sulfonamide bond. The precursor is a synthetic intermediate carrying a free —NH— which has been derivatized by the attachment of an electrophile via a sulfonamide bond.