Pirlimycin

Base Information

• Chemical Name: Pirlimycin
• CAS No.: 79548-73-5
• Molecular Formula: C₁₇H₃₁ClN₂O₅S
• Molecular Weight: 410.963
• UNII: LM19JT6G5K
• DSSTox Substance ID: DTXSID30904249
• Nikkaji Number: J32.482E
• Wikipedia: Pirlimycin
• Wikidata: Q7198039
• NCI Thesaurus Code: C84066
• Metabolomics Workbench ID: 144436
• ChEMBL ID: CHEMBL1652611
• Mol file: 79548-73-5.mol

Synonyms:cis-4-ethyl-L-picecolic acid amide of 7-deoxy-7(S)chloromethylthio lincosaminide hydrochloride;pirlimycin;pirlimycin monohydrochloride monohydrate, (2S-cis)-isomer;pirlimycin monohydrochloride, (2R-cis)-isomer;U 57930E;U-57930E

Chemical Property of Pirlimycin

Chemical Property:

• Vapor Pressure: 2.68E-19mmHg at 25°C
• Refractive Index: 1.574
• Boiling Point: 643.9 °C at 760 mmHg
• PKA: 12.88±0.70(Predicted)
• Flash Point: 343.2 °C
• PSA: 136.35000
• Density: 1.31 g/cm³
• LogP: 0.76700
• Solubility.: Soluble in ethanol;Soluble in methanol;Soluble in DMSO;Soluble in dimethyl formamide
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 410.1642210
• Heavy Atom Count: 26
• Complexity: 474

Purity/Quality:

99% ^*data from raw suppliers

Pirlimycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1CCNC(C1)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)Cl
• Isomeric SMILES: CC[C@@H]1CCN[C@@H](C1)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@H](C)Cl
• Uses: Pirlimycin is a semi-synthetic lincosamide prepared from clindamycin by hydrolysing the propyl N-methylproline and re-annealing a 4-ethylpipecolic acid. Pirlimycin is more hydrophobic than clindamycin and is more potent against a number of important pathogens. Like other members of the lincosamide family, pirlimycin is a broad spectrum antibiotic with activity against anaerobic bacteria and protozoans. Pirlimycin acts by binding to the 23S ribosomal subunit, blocking protein synthesis. Pirlimycin has been less extensively researched than the older lincosamides.

Technology Process of Pirlimycin

There total 3 articles about Pirlimycin 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:

4-ethyl-2-pyridinecarboxamide of methyl (7S)-7-chloro-7-deoxythiolincosamide (78788-60-0) → (2R-cis)-4-ethylpipecolamide of methyl (7S)-7-chloro-7-deoxythiolincosamide (78822-41-0) + Pirlimycin (79548-73-5)

Guidance literature:

With hydrogenchloride; hydrogen; platinum(IV) oxide; In methanol; at 25 ℃; for 18h; under 2585.7 Torr;

DOI:10.1021/jm00368a020

Reference yield:

methyl 6-amino-7(S)-chloro-6,7,8-trideoxy-1-thio-L-threo-α-D-galacto-octopyranoside (22965-79-3) → Pirlimycin (79548-73-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / acetone; H₂O; acetonitrile / 18 h / 25 °C

2: H₂, aq. HCl / PtO₂ / methanol / 18 h / 25 °C / 2585.7 Torr

With hydrogenchloride; hydrogen; platinum(IV) oxide; In methanol; water; acetone; acetonitrile;

DOI:10.1021/jm00368a020

Reference yield:

4-ethyl-2-pyridinecarboxylic 3-methylbutanoic anhydride (88015-20-7) → Pirlimycin (79548-73-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / acetone; H₂O; acetonitrile / 18 h / 25 °C

2: H₂, aq. HCl / PtO₂ / methanol / 18 h / 25 °C / 2585.7 Torr

With hydrogenchloride; hydrogen; platinum(IV) oxide; In methanol; water; acetone; acetonitrile;

DOI:10.1021/jm00368a020

upstream raw materials:

4-ethyl-2-pyridinecarboxamide of methyl (7S)-7-chloro-7-deoxythiolincosamide

methyl 6-amino-7(S)-chloro-6,7,8-trideoxy-1-thio-L-threo-α-D-galacto-octopyranoside

4-ethyl-2-pyridinecarboxylic 3-methylbutanoic anhydride

Refernces