(S)-(-)-pindolol

Base Information

• Chemical Name: (S)-(-)-pindolol
• CAS No.: 26328-11-0
• Molecular Formula: C14H20N2O2
• Molecular Weight: 248.325
• Hs Code.: 2933990090
• UNII: E34B58KY5W
• DSSTox Substance ID: DTXSID70873364
• Nikkaji Number: J221.536E
• Wikidata: Q27088394
• Pharos Ligand ID: RM3W9F1H1LSY
• Metabolomics Workbench ID: 56924
• ChEMBL ID: CHEMBL117405
• Mol file: 26328-11-0.mol

Synonyms:(S)-(-)-pindolol;26328-11-0;S(-)-Pindolol;(-)-pindolol;l-Pindolol;espindolol;(S)-pindolol;S(?)-Pindolol;Pindolol, (S)-;AGI-001;mt-102;CHEMBL117405;E34B58KY5W;(2S)-1-(1H-indol-4-yloxy)-3-(isopropylamino)propan-2-ol;CHEBI:48281;(2S)-1-(1H-indol-4-yloxy)-3-[(propan-2-yl)amino]propan-2-ol;(S)-1-(1H-indol-4-yloxy)-3-[(1-methylethyl)amino]-2-propanol;(2S)-1-(1H-indol-4-yloxy)-3-(propan-2-ylamino)propan-2-ol;(2S)-1-(1H-indol-4-yloxy)-3-[(1-methylethyl)amino]propan-2-ol;(S)-1-((1H-indol-4-yl)oxy)-3-(isopropylamino)propan-2-ol;2-Propanal, 1-(1H-indol-4-yloxy)-3-((1-methylethyl)amino)-, (S)-;2-Propanol, 1-(1H-indol-4-yloxy)-3-[(1-methylethyl)amino]-, (2S)-;SR-01000075488;2-PROPANOL, 1-(1H-INDOL-4-YLOXY)-3-((1-METHYLETHYL)AMINO)-, (2S)-;pindolol-(-);S-PINDOLOL;Tocris-1060;(-)-Pindolol;(S)-(-)-Pindolol;S-Pindolol;S(-)-Pindolol, solid;SCHEMBL5220;UNII-E34B58KY5W;Lopac0_000349;Lopac0_001027;GTPL127;MLS001056774;PINDOLOL (S -ISOMER);AGI001;AGI 001;DTXSID70873364;C14H29N2O2;HMS2231C09;HMS3261E19;HMS3267E06;HMS3412E05;HMS3676E05;MT102;Tox21_500349;BDBM50072755;MT 102;PDSP1_000743;PDSP2_000731;AKOS024456358;C14-H29-N2-O2;CCG-204444;LP00349;SDCCGSBI-0050337.P003;NCGC00024973-01;NCGC00024973-02;NCGC00024973-03;NCGC00024973-04;NCGC00024973-05;NCGC00261034-01;AC-36933;MS-23519;SMR000326991;HY-100606;CS-0019759;EU-0100349;EU-0101027;P-152;A899554;SR-01000597475;J-016382;SR-01000075488-1;SR-01000075488-2;SR-01000597475-1;BRD-K95598440-001-03-6;Q27088394;(S)-1-(1H-Indole-4-yloxy)-3-[(1-methylethyl)amino]-2-propanol;2-Propanal,1-(1H-indol-4-yloxy)-3-((1-methylethyl)amino)-,(S)-;2-PROPANOL, 1-(INDOL-4-YLOXY)-3-(ISOPROPYLAMINO)-, (-)-;2-propanol,1-(1h-indol-4-yloxy)-3-[(1-methylethyl)amino]-,(2s)-;(2S)-1-(1H-INDOL-4-YLOXY)-3-((1-METHYLETHYL)AMINO)-2-PROPANOL;2-PROPANOL, 1-(1H-INDOL-4-YLOXY)-3-((1-METHYLETHYL)AMINO)-, (S)-

Chemical Property of (S)-(-)-pindolol

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 3.77E-09mmHg at 25°C
• Refractive Index: 1.596
• Boiling Point: 457.1 °C at 760 mmHg
• PKA: 13.94±0.20(Predicted)
• Flash Point: 230.3 °C
• PSA: 57.28000
• Density: 1.152 g/cm³
• LogP: 2.29650
• Storage Temp.: Desiccate at +4°C
• Solubility.: 0.1 M NaOH: 0.2 mg/mL
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 248.152477885
• Heavy Atom Count: 18
• Complexity: 248

Purity/Quality:

99% ^*data from raw suppliers

(S)-(-)-Pindolol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)NCC(COC1=CC=CC2=C1C=CN2)O
• Isomeric SMILES: CC(C)NC[C@@H](COC1=CC=CC2=C1C=CN2)O
• Recent ClinicalTrials: A Clinical Study With MT-102 in Subjects With Cancer Cachexia
• Recent EU Clinical Trials: A multicentre, randomised, double-blind, placebo-controlled, dose-finding phase II study to evaluate the efficacy of two different doses of MT-102 administered over a sixteen week period in subjects with cachexia related to stage III and IV non-small cell lung cancer and colorectal cancer

Technology Process of (S)-(-)-pindolol

There total 26 articles about (S)-(-)-pindolol 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: 100.0%

(2R)-1-(1H-indol-4-yloxy)-3-chloro-2-propanol + isopropylamine (75-31-0) → (S)-pindolol (26328-11-0)

Guidance literature:

for 12h; Reflux;

DOI:10.1016/j.apcata.2017.08.003

Reference yield: 89.0%

(S)-(-)-1-<1-(4-methylphenyl)sulfonyl-4-indolyloxy>-3-(2-propylamino)-2-propanol (144024-36-2) → (S)-pindolol (26328-11-0)

Guidance literature:

With sodium hydroxide; In ethanol; for 14h; Heating;

DOI:10.1248/cpb.40.2353

Reference yield: 88.0%

acetone (67-64-1) + (S)-4-(2-hydroxy-3-nitropropoxy)indole (160319-71-1) → (+)-Pindolol (68374-35-6) + (S)-pindolol (26328-11-0)

Guidance literature:

With platinum(IV) oxide; hydrogen; In methanol; at 50 ℃; for 16h;

DOI:10.1016/S0040-4020(01)89540-5

upstream raw materials:

1-(1H-indol-4-yloxy)-3-(isopropylamino)-2-propanol

<5S>-3-isopropyl-5-(4-indolyloxymethyl)-oxazolidin-2-one

(S)-(-)-1-<1-(4-methylphenyl)sulfonyl-4-indolyloxy>-3-(2-propylamino)-2-propanol

isopropylamine

Downstream raw materials:

S-pindolol benzoate

Refernces

• 1、 Lima, Gledson Vieira,da Silva, Marcos Reinaldo,de Sousa Fonseca, Thiago,de Lima, Leandro Bezerra,de Oliveira, Maria da Concei??o Ferreira,de Lemos, Telma Leda Gomes,Zampieri, Davila,dos Santos, Jose Cleiton Sousa,Rios, Nathalia Saraiva,Gon?alves, Luciana Rocha Barros,Molinari, Francesco,de Mattos, Marcos Carlos. "Chemoenzymatic synthesis of (S)-Pindolol using lipases". . p. 7 - 14. Retrieved 2017.
• 2、 Sasai, Hiroaki,Yamada, Yoichi M. A.,Suzuki, Takeyuki,Shibasaki, Masakatsu. "Syntheses of (S)-(-)-Pindolol and -(R)-(-)-Pindolol Utilizing a Lanthanum-Lithium-(R)-BINOL ((R)-LLB) Catalyzed Nitroaldol Reaction". . p. 12313 - 12318. Retrieved 1994.
• 3、 Liu, Yi,Sombra, Lorena L.,Stege, Patricia W.. "Enantiomeric separation of β-blockers and tryptophan using heparin as stationary and pseudostationary phases in capillary electrophoresis". . p. 988 - 995. Retrieved 2018/07/29.