6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide

Base Information

• Chemical Name: 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide
• CAS No.: 49843-98-3
• Molecular Formula: C₁₃H₁₃ClN₂O
• Molecular Weight: 248.712
• Hs Code.: 2933998090
• European Community (EC) Number: 664-029-6
• UNII: L19ECD5014
• ChEMBL ID: CHEMBL420311
• DSSTox Substance ID: DTXSID10964442
• Metabolomics Workbench ID: 154707
• NCI Thesaurus Code: C152325
• Nikkaji Number: J2.607.557B
• Pharos Ligand ID: WW376M35S6J4
• Wikidata: Q27088776
• Mol file: 49843-98-3.mol

Synonyms:6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide;EX 527;EX-527;EX527 cpd;selisistat;SEN0014196

Chemical Property of 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide

Chemical Property:

• Melting Point: 179.0 to 183.0 °C
• Boiling Point: 531.717 °C at 760 mmHg
• PKA: 16.12±0.40(Predicted)
• Flash Point: 275.373 °C
• PSA: 58.88000
• Density: 1.389 g/cm³
• LogP: 3.42680
• Storage Temp.: Store at +4°C
• Solubility.: Soluble in dimethyl sulfoxide, ethanol and dimethyl formamide.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 248.0716407
• Heavy Atom Count: 17
• Complexity: 323

Purity/Quality:

98% ^*data from raw suppliers

Selisistat ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(C2=C(C1)C3=C(N2)C=CC(=C3)Cl)C(=O)N
• Recent ClinicalTrials: SIRT-1 Antagonism for Endometrial Receptivity
• Recent EU Clinical Trials: A double-blind, placebo-controlled study in Huntington’s Disease patients to determine the safety and tolerability of SEN0014196
• Description: EX-527 (49843-98-3) is a selective SIRT1 inhibitor (IC50=98 nM). Does not inhibit other HDACs or SIRT family members. Increases p53 acetylation following DNA damage. Cell permeable.
• Uses: EX-527 has been used:in 1% dimethyl sulfoxide, 30%, polyethylene glycol-400 and 1% Tween 80 for treating C57BL/6 N mice to study its effect on intestinal morphological changes and crypt cell apoptosisas a an inhibitor of sirtuin 1, in treating human cancer lines MCF-7 (Michigan cancer foundation-7) and HCT116 (colon cancer cell line) incubated in Dulbecco′s modified Eagle′s medium, to study its effect on mitochondrial ATP (adenosine triphosphate) productionIntracerebroventricularly infused in rat model of epileptogenesis, to access kainic acid–induced status epilepticus stimulated sirtuin 1 activity A selective inhibitor of SIRT1 over SIRT2 and SIRT3 EX-527 is a potent and selective sirtuin 1 (SIRT1) inhibitor (IC50 38 nM) identified from a high throughput screen. EX-527 is more selective (200-500-fold) for SIRT1 than for SIRT2 or SIRT3 and has been shown to be a potent SIRT6 inhibitor using H3K56 deacetylation site based substrate. EX-527 does not inhibit class I/II HDAC activity at concentrations up to 100uM. Enhances p53 acetylation in response to DNA damaging agents. EX-527 is racemic; the active isomer (EX-243) gives similar results and potency whereas the other isomer (designated EX-242) is inactive.

Technology Process of 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide

There total 6 articles about 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide 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: 78.0%

6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylic acid ethyl ester (49844-36-2) → 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide (49843-98-3)

Guidance literature:

With ammonia; In ethanol; at 60 ℃; for 24h;

DOI:10.1021/jm050522v

Reference yield: 71.0%

6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylic acid (1-phenylethyl)amide (871586-78-6) → 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide (49843-98-3)

Guidance literature:

With sulfuric acid; at 20 ℃; for 2h;

DOI:10.1021/jm050522v

Reference yield:

ethyl 2-oxocyclohexane carboxylate (1655-07-8) → 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide (49843-98-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / Br₂ / diethyl ether / 1.5 h / 0 - 20 °C

2: 77 percent / 3 h / 150 °C

3: 91 percent / aq. NaOH / ethanol / 1 h / 20 °C

4: 64 percent / EDC; HOBt / CH₂Cl₂ / 20 °C

5: 71 percent / H₂SO₄ / 2 h / 20 °C

With sodium hydroxide; sulfuric acid; bromine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In diethyl ether; ethanol; dichloromethane;

DOI:10.1021/jm050522v

upstream raw materials:

6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylic acid (1-phenylethyl)amide

6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylic acid ethyl ester

6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylic acid

ethyl 3-bromo-2-oxocyclohexanecarboxylate

Refernces

• 1、 -. "PROCESSES FOR THE PREPARATION OF 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE AND OF ITS PRECURSORS". Page/Page column 13. . Retrieved 2013/05/09.
• 2、 -. "Treating a viral disorder". Page/Page column 20. . Retrieved 2008/06/13.