Indicine N-oxide

Base Information

• Chemical Name: Indicine N-oxide
• CAS No.: 41708-76-3
• Molecular Formula: C15H25NO6
• Molecular Weight: 315.367
• NSC Number: 132319
• DSSTox Substance ID: DTXSID101315334
• Nikkaji Number: J584.795H
• Wikidata: Q104985441
• NCI Thesaurus Code: C1134
• ChEMBL ID: CHEMBL512655
• Mol file: 41708-76-3.mol

Synonyms:indicine-N-oxide;NSC 132319

Chemical Property of Indicine N-oxide

Chemical Property:

• Melting Point: 130.5°C (rough estimate)
• Refractive Index: 1.5000 (estimate)
• Boiling Point: °Cat760mmHg
• PKA: 12.54±0.29(Predicted)
• Flash Point: °C
• PSA: 116.42000
• Density: g/cm³
• LogP: -0.35590
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 315.16818752
• Heavy Atom Count: 22
• Complexity: 479

Purity/Quality:

99% ^*data from raw suppliers

Indicine N-Oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(C)O)(C(=O)OCC1=CC[N+]2(C1C(CC2)O)[O-])O
• Isomeric SMILES: C[C@@H]([C@](C(C)C)(C(=O)OCC1=CC[N+]2([C@H]1[C@@H](CC2)O)[O-])O)O
• Description: Heliotropiurn indicurn also contains this base which has the structure given above based upon comparison with the preceding alkaloid. The base has proved to be highly active against transplanted neoplasts, Walker-256 carcinosarcoma, melanoma B-16, leukaemia L-12l 0, leukaemia P-388 and leukaemia P-1534 in mice and rats, giving up to 91 per cent inhibition of transplanted growth at a daily dosage of 200 mgm. per kilo.
• Uses: Indicine N-oxide is a pyrrolizidine alkaloid that is isolated from Heliotropium indicum, one of the most widely used herbs in India. Indicine N-oxide exhibits antitumour and antimitotic activity in humans, and has subsequently undergone Phase I & II trials in adults and children with leukemia and solid tumours.

Technology Process of Indicine N-oxide

There total 13 articles about Indicine N-oxide 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: 81.0%

(+)-indicine (480-82-0,26131-12-4) → (+)-indicine N-oxide (41708-76-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In acetone; for 2h; Ambient temperature;

DOI:10.1016/S0040-4039(01)80561-X

Reference yield:

(1'S,2S,5R)-2-(t-butyl)-5-(1'hydroxyethyl)-5-isopropyl-1,3-dioxolan-4-one (132585-75-2) → (+)-indicine N-oxide (41708-76-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 9.3 percent / camphorsulfonic acid / benzene / 72 h / Heating

2: 1) DCC, DMAP, 2) 1 M HCl / 1) toluene, r.t., 6 d, 2) r.t., 28 h

3: 81 percent / m-chloroperoxybenzoic acid / acetone / 2 h / Ambient temperature

With hydrogenchloride; dmap; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; camphor-10-sulfonic acid; In acetone; benzene;

DOI:10.1016/S0040-4020(01)80345-8

Reference yield:

(2R,3S)-2,3-dihydroxy-2-(1-methylethyl)butyric acid (23944-50-5) → (+)-indicine N-oxide (41708-76-3)

Guidance literature:

Multi-step reaction with 3 steps

1: concd hydrochloric acid / Ambient temperature

2: 1.) DCC, DMAP; 2.) 0.6 M HCl / 1.) toluene, r.t., 3 d; 2.) r.t., 8 h

3: MCPBA / acetone / 1 h / Ambient temperature

With hydrogenchloride; dmap; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In acetone;

DOI:10.1246/bcsj.60.4107

upstream raw materials:

(+)-indicine

(2R,3S)-2,3-dihydroxy-2-(1-methylethyl)butyric acid

4(R)-(1-methylethyl)-2,2,5(S)-trimethyl-1,3-dioxolane-4-carboxylic acid

(1'S,2S,5R)-2-(t-butyl)-5-(1'hydroxyethyl)-5-isopropyl-1,3-dioxolan-4-one

Downstream raw materials:

lycopsamine A

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