| Identification | Back Directory | [Name]
9-Nitrocamptothecin | [CAS]
86639-62-5 | [Synonyms]
RUBETICAN
9-NITRO-CPT
9-Nitro-20(S)-camptothecine
CAMPTOTHECIN, 9-NITRO-20(S)-
10-Nitrocamptothecin ISO 9001：2015 REACH
4α-Ethyl-4-hydroxy-10-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
(S)-4-Ethyl-4-hydroxy-10-nitro-1H-pyrano[3',4':6,7]-indolizino[1,2-b]quinoline-3,14(4H,12H)-di
(S)-4-Ethyl-4-hydroxy-9-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
(S)-4-Ethyl-4-hydroxy-10-nitro-1H-pyrano[3',4':6,7]-indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-9-nitro-, (4S)- | [Molecular Formula]
C20H15N3O6 | [MDL Number]
MFCD06656294 | [MOL File]
86639-62-5.mol | [Molecular Weight]
393.35 |
| Questions And Answer | Back Directory | [Synthesis]
20(S)-10-Nitrocamptothecin was synthesized using a mixed nitrating agent. Camptothecin was used as the raw material, concentrated sulfuric acid as the reaction medium, and mixed nitrates as the nitrating agent for the nitration reaction. The target product, 9-NC, was then obtained by chromatographic separation and purification. The yield of 9-NC was increased from 31% to approximately 40%. The optimal process conditions obtained were: 0.5 g camptothecin, 30 ml concentrated sulfuric acid; 0.007 mol nitrate; a molar ratio of ammonium nitrate to calcium nitrate of 1:1; a reaction temperature of 20℃; and a reaction time of 1 day. This method has the advantages of high yield and easy separation and purification. The specific reaction process is as follows:  |
| Hazard Information | Back Directory | [Uses]
Whether cells can divide depends on the two key points of entering S phase and M phase. Studies have found that 10-Nitrocamptothecin can induce apoptosis. After administration, both S phase and G2M phase of cell growth are delayed. Inhibition occurred throughout the cell cycle and was found to be dose- and time-dependent. | [Definition]
ChEBI:Rubitecan is a pyranoindolizinoquinoline that is camptothecin in which the hydrogen at position 9 has been replaced by a nitro group. It is a prodrug for 9-aminocamptothecin. It has a role as an antineoplastic agent, an EC 5.99.1.2 (DNA topoisomerase) inhibitor and a prodrug. It is a pyranoindolizinoquinoline, a C-nitro compound, a semisynthetic derivative, a tertiary alcohol and a delta-lactone. |
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