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              Name Rubitecan;9-Nitrocamptothecin;9-NC;RFS-2000;Orathecin;Camptogen
              Chemical Name 9-Nitro-20(S)-camptothecin
                    4(S)-Ethyl-4-hydroxy-10-nitro-1H-pyrano[3,4:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
              CAS 91421-42-0
              Related CAS
              Formula C20H15N3O6
              Structure
              Formula Weight 393.35905
              Stage 預注冊
              Company SuperGen (Orphan Drug), Stehlin Foundation for Cancer Research (Originator), SuperGen (Licensee)
              Activity/Mechanism AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY, Brain Cancer Therapy, Breast Cancer Therapy, Colorectal Cancer Therapy, Head and Neck Cancer Therapy, Leukemia Therapy, Lung Cancer Therapy, Lymphoma Therapy, Melanoma Therapy, Myelodysplastic Syndrome Therapy, Oncolytic Drugs, Ovarian Cancer Therapy, Pancreatic Cancer Therapy, Prostate Cancer Therapy, Solid Tumors Therapy, Camptothecins, DNA Topoisomerase I Inhibitors
              Syn. Route 1
              Route 1
              this compound can be obtained in two different ways:1) by direct nitration of camptothecin (i) with nitric acid in sulfuric acid.2) by direct nitration of camptothecin (i) with different inorganic nitrates (or mixtures of inorganic nitrates) in sulfuric acid.3) the reaction of 2,6-dinitrobenzaldehyde (ii) with ethylene glycol (iii) and p-toluenesulfonic acid in refluxing toluene gives the corresponding ethylene ketal (iv), which is reduced with sodium sulfide in refluxing ehanol/water yielding 2-amino-6-nitrobenzaldehyde ethylene ketal (v). the hydrolysis of (v) with aqueous sulfuric acid affords 2-amino-6-nitrobenzaldehyde (vi), which is finally cyclized with the tricyclic ketone (vii) in refluxing acetic acid (the same cyclization can be performed with the ketal (v) and the ketone (vii).
              List of intermediates No.
              (10s,11r,12s)-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-11,12-dihydro-2h,6h,10h-dipyrano[2,3-f:2,3-h]chromen-2-one (i)
              tert-butyl 2-[(1-[(2s)-2-[[(benzyloxy)carbonyl]amino]-3-[4-(tert-butoxy)phenyl]propanoyl]-4-piperidinyl)oxy]acetate (vii)
              (1r,4as,10ar)-7-isopropyl-1,4a-dimethyl-6-sulfo-1,2,3,4,4a,9,10,10a-octahydro-1-phenanthrenecarboxylic acid (iii)
              3-(1-piperazinyl)propanamide (vi)
              (2-iodoethenyl)(trimethyl)silane (ii)
              (iv)
              methyl 2-{(2r,4as,6s,7s,8r,8ar)-7,8-dihydroxy-6-[(e)-1-hydroxy-3-(trimethylsilyl)-2-propenyl]octahydropyrano[3,2-b]pyran-2-yl}acetate (v)
              Reference 1:
                  cao, z.s.; et al.; nitration of campothecin with various inorganic nitrate salts in concentrated sulfuric acid: a new preparation of anticancer drug 9-nitrocamptothecin. synthesis 1998, 12, 1724.
              Reference 2:
                  sawada, s.; matsuoka, s.-i.; nokata, k.-i.; nagata, h.; furuta, t.; yokokura, t.; miyasaka, t.; synthesis and antitumor activity of 20(s)-camptothecin derivatives: a-ring modified and 7,10-disubstituted camptothecins. chem pharm bull 1991, 39, 12, 3183.
              Reference 3:
                  wani, m.c.; nicholas, a.w.; wall, m.e.; plant antitumor agents. 23. synthesis and antileukemic activity of camptothecin analogues. j med chem 1986, 29, 11, 2358.
              Reference 4:
                  leitner, p.; tele, c.; truesdale, a.; nicholas, a.w.; moore, l.; besterman, j.m.; manikumar, g.; wani, m.c.; wall, m.e.; plant antitumor agents. 30. synthesis and structure activity of novel camptothecin analogs. j med chem 1993, 36, 18, 2689.

              來源:藥化網

              作者:藥化小編

              摘要:本文合成路線介紹的是藥物中文名魯比特康;英文名Rubitecan;9-Nitrocamptothecin;9-NC;RFS-2000;Orathecin;Camptogen;CAS[91421-42-0]

               
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