(S)-4-Ethyl-4-hydroxy-9-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione

Base Information

• Chemical Name: (S)-4-Ethyl-4-hydroxy-9-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
• CAS No.: 86639-62-5
• Molecular Formula: C20H15 N3 O6
• Molecular Weight: 393.356
• DSSTox Substance ID: DTXSID801016567
• Nikkaji Number: J448.360J
• Pharos Ligand ID: DKZ869R8Z2QP
• ChEMBL ID: CHEMBL2115022
• Mol file: 86639-62-5.mol

Synonyms:(S)-4-Ethyl-4-hydroxy-9-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;CHEMBL2115022;10-nitro-camptothecin;(19S)-19-ethyl-19-hydroxy-7-nitro-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione;9-Nitrocamptothecine;SCHEMBL5319149;DTXSID801016567;BCP10552;BDBM50406993

Chemical Property of (S)-4-Ethyl-4-hydroxy-9-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione

Chemical Property:

• Boiling Point: 827.4±65.0 °C(Predicted)
• PKA: 11.17±0.20(Predicted)
• PSA: 127.24000
• Density: 1.63±0.1 g/cm3(Predicted)
• LogP: 2.51100
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 393.09608521
• Heavy Atom Count: 29
• Complexity: 861

Purity/Quality:

97% ^*data from raw suppliers

(S)-4-Ethyl-4-hydroxy-10-nitro-1H-pyrano[3',4':6,7]-indolizino[1,2-b]quinoline-3,14(4H,12H)-dione 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(C2=C(COC1=O)C(=O)N3CC4=C(C3=C2)N=C5C=CC(=CC5=C4)[N+](=O)[O-])O
• Isomeric SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=C(C3=C2)N=C5C=CC(=CC5=C4)[N+](=O)[O-])O

Technology Process of (S)-4-Ethyl-4-hydroxy-9-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione

There total 7 articles about (S)-4-Ethyl-4-hydroxy-9-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-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: 86.0%

2-amino-5-nitrobenzaldehyde (56008-61-8) + (4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione (110351-94-5) → 10-nitro-(20S)-camptothecin (86639-62-5)

Guidance literature:

With hydrogenchloride; acetic acid; for 10h; Heating;

DOI:10.1021/jm00070a013

Reference yield:

Camptothecin 1-oxide (86639-48-7) → 10-nitro-(20S)-camptothecin (86639-62-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 11.5 percent / 1 N aq. H₂SO₄ / dioxane / 0.5 h / Irradiation

2: H₂, acetic acid / PtO₂ / dioxane / 760 Torr

3: 98 percent / pyridine / 1 h / 70 °C

4: 96.3 percent / H₂SO₄, conc. aq. HNO₃ / 1 h

5: 82.3 percent / 20percent aq. H₂SO₄ / 2 h / Heating

6: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / dioxane / 2 h / Heating

With pyridine; sulfuric acid; hydrogen; nitric acid; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; platinum(IV) oxide; In 1,4-dioxane;

DOI:10.1248/cpb.39.3183

Reference yield:

camptothecin (7689-03-4,91926-09-9) → 10-nitro-(20S)-camptothecin (86639-62-5)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂, acetic acid / PtO₂ / dioxane / 760 Torr

2: 98 percent / pyridine / 1 h / 70 °C

3: 96.3 percent / H₂SO₄, conc. aq. HNO₃ / 1 h

4: 82.3 percent / 20percent aq. H₂SO₄ / 2 h / Heating

5: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / dioxane / 2 h / Heating

With pyridine; sulfuric acid; hydrogen; nitric acid; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; platinum(IV) oxide; In 1,4-dioxane;

DOI:10.1248/cpb.39.3183

upstream raw materials:

2-amino-5-nitrobenzaldehyde

(4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione

(4R,5bS,11aS)-4-Ethyl-4-hydroxy-9-nitro-1,5b,6,11,11a,12-hexahydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

Camptothecin 1-oxide

Downstream raw materials:

10-amino-20(S)-camptothecin

10-methoxycamptothecin

(S)-10-hydroxycamptothecin