Caspase-3/7 Inhibitor I

Base Information

• Chemical Name: Caspase-3/7 Inhibitor I
• CAS No.: 220509-74-0
• Molecular Formula: C14H16N2O5S
• Molecular Weight: 324.357
• DSSTox Substance ID: DTXSID50431688
• Nikkaji Number: J1.319.413K
• Wikidata: Q82245641
• Pharos Ligand ID: RMMW9VG71B55
• ChEMBL ID: CHEMBL60190
• Mol file: 220509-74-0.mol

Synonyms:Caspase-3/7 Inhibitor I;220509-74-0;MMPSI;Caspase-3/7 Inhibitor;CHEMBL60190;5-[(S)-(+)-2-(Methoxymethyl)pyrrolidino]sulfonylisatin;5-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]sulfonyl-1H-indole-2,3-dione;Pyrrolidine,1-[(2,3-dihydro-2,3-dioxo-1H-indol-5-yl)sulfonyl]-2-(MethoxyMethyl)-,(2S)-;Isatin Sulfonamide 16;SCHEMBL3681388;BDBM10305;DTXSID50431688;SLQMNVJNDYLJSF-VIFPVBQESA-N;VIA50974;AKOS040744939;HY-103346;CS-0027695;A14919;Caspase-3/7 Inhibitor I - CAS 220509-74-0;J-014451;(S)-5-[1-(2-Methoxymethyl)pyrrolidinylsulfonyl]isatin;5-[[(2S)-2-(Methoxymethyl)pyrrolizino]sulfonyl]indoline-2,3-dione;5-{[(2S)-2-(Methoxymethyl)pyrrolidin-1-yl]sulfonyl}-1H-indole-2,3-dione;5-{[(2S)-2-(methoxymethyl)pyrrolidine-1-]sulfonyl}-2,3-dihydro-1H-indole-2,3-dione

Chemical Property of Caspase-3/7 Inhibitor I

Chemical Property:

• PKA: 8.66±0.20(Predicted)
• PSA: 101.16000
• Density: 1.415±0.06 g/cm3(Predicted)
• LogP: 1.77760
• Solubility.: insoluble in H2O; ≥16.2 mg/mL in DMSO; ≥2.17 mg/mL in EtOH with gentle warming and ultrasonic
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 324.07799279
• Heavy Atom Count: 22
• Complexity: 570

Purity/Quality:

99% ^*data from raw suppliers

Caspase-3/7InhibitorI ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCC1CCCN1S(=O)(=O)C2=CC3=C(C=C2)NC(=O)C3=O
• Isomeric SMILES: COC[C@@H]1CCCN1S(=O)(=O)C2=CC3=C(C=C2)NC(=O)C3=O

Technology Process of Caspase-3/7 Inhibitor I

There total 8 articles about Caspase-3/7 Inhibitor I 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: 93.0%

(2S)-2-(methoxymethyl)-1-pyrrolidine (63126-47-6) + 5-chlorosulfonylisatin (132898-96-5) → (S)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin (220509-74-0,1110670-49-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; chloroform; at 0 ℃; for 1.5h;

Reference yield:

(S)-3,3-dichloro-5-(2-(methoxymethyl)pyrrolidin-1-ylsulfonyl)indolin-2-one (220428-23-9) → (S)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin (220509-74-0,1110670-49-9)

Guidance literature:

In water; acetic acid; at 90 ℃;

DOI:10.1016/j.bmcl.2011.01.110

Reference yield:

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → (S)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin (220509-74-0,1110670-49-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: H₂SO₄; SO₃ / -15 - 70 °C

1.2: 83 percent / aq. NaOH / pH 7 / cooling

2.1: 67 percent / tetramethylene sulfone; POCl₃ / 3 h / 60 °C

3.1: 2.05 g / N,N-diisopropylethylamine / tetrahydrofuran; CHCl₃ / 0.5 h

With sulfolane; sulfuric acid; sulfur trioxide; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In tetrahydrofuran; chloroform;

DOI:10.1021/jm051217c

upstream raw materials:

(2S)-2-(methoxymethyl)-1-pyrrolidine

5-chlorosulfonylisatin

2-methoxymethylpyrrolidine-1-carboxylic acid tert-butyl ester

N-(tert-butoxycarbonyl)-L-prolinol

Downstream raw materials:

1-(4-iodobenzyl)-5-(2(S)-methoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione

(S)-1-(p-tert-butyldimethylsilyloxybenzyl)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin

(S)-1-(4-(2-bromoethoxy)benzyl)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin

(S)-1-(4-(2-(p-methylphenylsulfonyloxy)ethoxy)benzyl)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin