(7S,9S)-7-[[(4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-9-(2-hydroxy-1-oxoethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione

Base Information

• Chemical Name: (7S,9S)-7-[[(4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-9-(2-hydroxy-1-oxoethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• CAS No.: 23214-92-8
• Molecular Formula: C27H29NO11
• Molecular Weight: 543.527
• Hs Code.: 2941900000
• NSC Number: 759155
• Wikidata: Q27163556
• Mol file: 23214-92-8.mol

Synonyms:SCHEMBL1898193;CHEBI:91746;HMS2093N11;Pharmakon1600-01505483;NSC759155;CCG-213465;SBI-0206795.P001;AB01563319_01;SR-05000001645;SR-05000001645-1;BRD-A52530684-001-01-1;BRD-A52530684-003-01-7;Q27163556;(7S,9S)-7-[(4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;(7S,9S)-7-[[(4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-9-(2-hydroxy-1-oxoethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione

Chemical Property of (7S,9S)-7-[[(4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-9-(2-hydroxy-1-oxoethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione

Chemical Property:

• Appearance/Colour: orange to red powder
• Vapor Pressure: 9.64E-28mmHg at 25°C
• Melting Point: 205 °C
• Refractive Index: 1.709
• Boiling Point: 810.293 °C at 760 mmHg
• PKA: pKa 8.2 (Uncertain)
• Flash Point: 443.849 °C
• PSA: 206.07000
• Density: 1.615 g/cm³
• LogP: 1.50360
• Storage Temp.: -20°C
• Solubility.: ≥27.2 mg/mL in DMSO; insoluble in EtOH; ≥24.8 mg/mL in H2O with ultrasonic
• Water Solubility.: Soluble
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 5
• Exact Mass: 543.17406074
• Heavy Atom Count: 39
• Complexity: 977

Purity/Quality:

99%, ^*data from raw suppliers

PK2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O
• Isomeric SMILES: C[C@H]1[C@H]([C@H](CC(O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O
• Uses: Doxorubicin is one of the most effective neoplastic drugs, and is mainly used in combination with other drugs for treating solid tumors. This drug is used for leukemia, various sarcomas, practically every type of cancer, neuroblastomas, leukoses, and lymphomas. Doxorubicin USP (Adriamycin) is used to traet soft-tissue and osteogenic sarcomas; Hodgkin’s disease; non-Hodgkin’s lymphomas; acute leukemia; cancer of thyroid, breast, lung, genitourinary (GU) tract; Wilm’s tumor; neuroblastoma. Doxorubicin (adriamycin) is the most extensively studied of a family of highly fluorescent anthracycline antibiotics produced by several Streptomyces species, first reported in 1967 and later approved for human therapeutic use as an antitumour agent for the treatment of a wide range of cancers. Doxorubicin also exhibits anti-HIV and antibacterial activity. The mode of action of doxorubicin is thought to be due to intercalation of DNA and inhibition of nucleic acid synthesis.
• Indications: Doxorubicin binds tightly to DNA by its ability to intercalate between base pairs and therefore is preferentially concentrated in nuclear structures. Intercalation results in steric hindrance, hence production of single-strand breaks in DNA and inhibition of DNA synthesis and DNA-dependent RNA synthesis. The enzyme topoisomerase II is thought to be involved in the generation of DNA strand breaks by the anthracyclines. Cells in S-phase are most sensitive to doxorubicin, although cytotoxicity also occurs in other phases of the cell cycle.
• Therapeutic Function: Cancer chemotherapy
• Clinical Use: Doxorubicin is one of the most effective agents used in the treatment of carcinomas of the breast, ovary, endometrium, bladder, and thyroid and in oat cell cancer of the lung. It is included in several combination regimens for diffuse lymphomas and Hodgkin’s disease. Doxorubicin can be used as an alternative to daunorubicin in acute leukemias and is useful in Ewing’s sarcoma, osteogenic sarcoma, soft-tissue sarcomas, and neuroblastoma. Some activity has been reported in non–oat cell lung cancer, multiple myeloma, and adenocarcinomas of the stomach, prostate, and testis.

Technology Process of (7S,9S)-7-[[(4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-9-(2-hydroxy-1-oxoethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione

There total 85 articles about (7S,9S)-7-[[(4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-9-(2-hydroxy-1-oxoethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione 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: 100.0%

doxorubicin hydrochloride (25316-40-9) → doxorubicin (23214-92-8)

Guidance literature:

With triethylamine; In chloroform; at 25 ℃; for 24h; Darkness;

DOI:10.1021/ja505344t

Reference yield: 61.7%

Fmoc-GFLGG-Dox → doxorubicin (23214-92-8) + Fmoc-GFLGG-NHNH2

Guidance literature:

In aq. acetate buffer; at 37 ℃; for 96h; pH=5; pH-value; Solvent;

DOI:10.1002/asia.201601704

Reference yield:

C72H69N7O29 (1353003-29-8) → doxorubicin (23214-92-8) + 4-hydroxymethyl-2-nitrophenol (41833-13-0) + C8H9NO (1353003-34-5) + C30H27N5O5 (1353003-32-3) + C30H29N5O6 (1353003-33-4) + C66H61N7O23 (1353003-30-1) + Entinostat (209783-80-2,442532-99-2)

Guidance literature:

With Escherichia coli β-glucuronidase; at 37 ℃; for 0.5h; pH=7; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1002/cmdc.201100355

upstream raw materials:

Doxo-MBS

N-[4-O-β-D-glucuronyl-3-nitrobenzyloxycarbonyl]doxorubicin

doxazolidine

pro-Dox

Downstream raw materials:

N-(pentafluoropropionyl)adriamycin

N-Trifluoroacetyladriamycin

(8S,10S)-10-((2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-6,8,11-trihydroxy-8-(2-hydroxy-acetyl)-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione

doxorubicinol

Refernces

• 1、 Gu, Dunyin,Tan, Shereen,O'Connor, Andrea J.,Qiao, Greg G.. "On-Demand Cascade Release of Hydrophobic Chemotherapeutics from a Multicomponent Hydrogel System". . p. 1696 - 1707. Retrieved 2018.
• 2、 Vrudhula, Vivekananda M.,Svensson, Hakan P.,Senter, Peter D.. "Cephalosporin Derivatives of Doxorubicin as Prodrugs for Activation by Monoclonal Antibody-β-Lactamase Conjugates". . p. 1380 - 1385. Retrieved 1995.
• 3、 Zhang, Xuanmiao,Sun, Xun,Li, Jilong,Zhang, Xiaoning,Gong, Tao,Zhang, Zhirong. "Lipid nanoemulsions loaded with doxorubicin-oleic acid ionic complex: Characterization, in vitro and in vivo studies". . p. 496 - 505. Retrieved 2011.
• 4、 Jang, Joo Hee,Lee, Hoyeon,Sharma, Amit,Lee, Sang Min,Lee, Tae Hoon,Kang, Chulhun,Kim, Jong Seung. "Indomethacin-guided cancer selective prodrug conjugate activated by histone deacetylase and tumour-associated protease". . p. 9965 - 9968. Retrieved 2016.
• 5、 Post, Glen C.,Barthel, Benjamin L.,Burkhart, David J.,Hagadorn, John R.,Koch, Tad H.. "Doxazolidine, a proposed active metabolite of doxorubicin that cross-links DNA". . p. 7648 - 7657. Retrieved 2005.
• 6、 Cao, Yu,Hu, Xiao-Yu,Li, Yan,Zou, Xiaochun,Xiong, Shuhan,Lin, Chen,Shen, Ying-Zhong,Wang, Leyong. "Multistimuli-responsive supramolecular vesicles based on water-soluble pillar[6]arene and SAINT complexation for controllable drug release". . p. 10762 - 10769. Retrieved 2014.
• 7、 Lelieveldt, Lianne P.W.M.,Eising, Selma,Wijen, Abel,Bonger, Kimberly M.. "Vinylboronic acid-caged prodrug activation using click-to-release tetrazine ligation". . p. 8816 - 8821. Retrieved 2019.
• 8、 Yuan, Zhefan,Yi, Xiaoqing,Zhang, Jing,Cheng, Sixue,Zhuo, Renxi,Li, Feng. "A prodrug nanoassembly entrapping drugs as a tumor-targeted delivery system". . p. 801 - 803. Retrieved 2013.
• 9、 Ibsen, Stuart,Zahavy, Eran,Wrasidlo, Wolf,Hayashi, Tomoko,Norton, John,Su, Yongxuan,Adams, Stephen,Esener, Sadik. "Localized in vivo activation of a photoactivatable doxorubicin prodrug in deep tumor tissue". . p. 698 - 708. Retrieved 2013.
• 10、 Abou Taleb, Heba A.,El-Menshawe, Shahira F.,Omar, Hany A.,Saweris, Mina A.,Sayed, Ossama M.,Zaher, Dana M.. "The use of new quinazolinone derivative and doxorubicin loaded solid lipid nanoparticles in reversing drug resistance in experimental cancer cell lines: A systematic study". . . Retrieved 2020.