10-HYDROXY-9-NITROCAMPTOTHECIN

Base Information

• Chemical Name: 10-HYDROXY-9-NITROCAMPTOTHECIN
• CAS No.: 104267-73-4
• Molecular Formula: C20H15 N3 O7
• Molecular Weight: 409.355
• Mol file: 104267-73-4.mol

Synonyms:1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione,4-ethyl-4,9-dihydroxy-10-nitro-, (S)-; 9-Hydroxy-10-nitrocamptothecin

Chemical Property of 10-HYDROXY-9-NITROCAMPTOTHECIN

Chemical Property:

• Vapor Pressure: 7.58E-29mmHg at 25°C
• Melting Point: 205-208℃
• Boiling Point: 825.3°Cat760mmHg
• Flash Point: 452.9°C
• PSA: 147.47000
• Density: 1.71g/cm³
• LogP: 2.21660

Purity/Quality:

98%,99%, ^*data from raw suppliers

9-NITRO-10-HYDROXYCAMPTOTHECIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 10-HYDROXY-9-NITROCAMPTOTHECIN

There total 3 articles about 10-HYDROXY-9-NITROCAMPTOTHECIN 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: 83.0%

(S)-10-hydroxycamptothecin (19685-09-7,64439-81-2) → 9-nitro-10-hydroxy-20(S)-camptothecin (104267-73-4)

Guidance literature:

With nitric acid; In sulfuric acid; Ambient temperature;

DOI:10.1016/0960-894X(96)00083-2

Reference yield:

camptothecin (7689-03-4,91926-09-9) → 9-nitro-10-hydroxy-20(S)-camptothecin (104267-73-4)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂; AcOH / PtO₂ / dimethylsulfoxide

2: PhI(OAc)2; aq. AcOH

3: 83 percent / HNO₃; AcOH / ethyl acetate / 1 h

With [bis(acetoxy)iodo]benzene; hydrogen; nitric acid; acetic acid; platinum(IV) oxide; In dimethyl sulfoxide; ethyl acetate;

DOI:10.1055/s-2006-942359

Reference yield:

1,2,6,7-tetrahydro-(20S)-camphthotecine (870527-52-9) → 9-nitro-10-hydroxy-20(S)-camptothecin (104267-73-4)

Guidance literature:

Multi-step reaction with 2 steps

1: PhI(OAc)2; aq. AcOH

2: 83 percent / HNO₃; AcOH / ethyl acetate / 1 h

With [bis(acetoxy)iodo]benzene; nitric acid; acetic acid; In ethyl acetate;

DOI:10.1055/s-2006-942359

upstream raw materials:

(S)-10-hydroxycamptothecin

camptothecin

1,2,6,7-tetrahydro-(20S)-camphthotecine

Downstream raw materials:

rubitecan

9-amino-20(S)-camptothecin

4-methoxy-benzenesulfonic acid 4-ethyl-4-hydroxy-10-nitro-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester

4-fluoro-benzenesulfonic acid 4-ethyl-4-hydroxy-10-nitro-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester

Refernces

• 1、 Pan, Peichen,Chen, Jiean,Li, Xijian,Li, Miyang,Yu, Huidong,Zhao, Jean J.,Ni, Jing,Wang, Xuwen,Sun, Huiyong,Tian, Sheng,Zhu, Feng,Liu, Feng,Huang, Yong,Hou, Tingjun. "Structure-Based Drug Design and Identification of H2O-Soluble and Low Toxic Hexacyclic Camptothecin Derivatives with Improved Efficacy in Cancer and Lethal Inflammation Models in Vivo". . p. 8613 - 8624. Retrieved 2018.
• 2、 Fu, Qingquan,Chen, Zhiyong. "A practical regiospecific synthesis of 9-nitrocamptothecin". . p. 1940 - 1942. Retrieved 2007/10/03.