64140-62-1

Basic information

• Product Name: 3-CHLORO-1-(2,3-DIHYDRO-1H-INDOL-1-YL)PROPAN-1-ONE
• Synonyms: 3-CHLORO-1-(2,3-DIHYDRO-1H-INDOL-1-YL)PROPAN-1-ONE;AKOS 90912;1-(3-CHLOROPROPANOYL)INDOLINE;3-Chloro-1-(2,3-dihydro-1H-indol-1-yl)propan-1-one, tech;3-chloro-1-(1-indolinyl)propan-1-one;3-chloro-1-(2,3-dihydroindol-1-yl)propan-1-one;3-CHLORO-1-(2,3-DIHYDRO-1H-INDOL-1-YL)PROPAN-1-ON
• CAS NO: 64140-62-1
• Molecular Formula: C₁₁H₁₂ClNO
• Molecular Weight: 209.67
• Mol File: 64140-62-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 83 °C
• Appearance: /
• CAS DataBase Reference: 3-CHLORO-1-(2,3-DIHYDRO-1H-INDOL-1-YL)PROPAN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-1-(2,3-DIHYDRO-1H-INDOL-1-YL)PROPAN-1-ONE(64140-62-1)
• EPA Substance Registry System: 3-CHLORO-1-(2,3-DIHYDRO-1H-INDOL-1-YL)PROPAN-1-ONE(64140-62-1)

Safety Data

• Hazardous Substances Data: 64140-62-1(Hazardous Substances Data)

Upstream product

• 496-15-1 1-indoline 
• 625-36-5 2-chloropropionyl chloride 

Downstream Products

• 1194451-12-1 1,2,5,6-tetrahydro-8-(hydroxy(phenyl)(pyridin-4-yl)methyl)pyrrolo[3,2,1-ij]quinolin-4-one 
• 1194451-14-3 1,2,5,6-tetrahydro-8-(phenyl(pyridin-4-yl)methyl)pyrrolo[3,2,1-ij]quinolin-4-one 
• 1616622-82-2 8-(5-(2-(4-methylbenzenesulfonyl)oxy)ethyloxypyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one 
• 1301160-23-5 8-benzoyl-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one 
• 1301160-24-6 8-(hydroxy-phenyl-methyl)-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one 
• 1194450-79-7 8-[(1H-imidazol-1-yl)(phenyl)methyl]-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinolin-4-one 
• 1386443-21-5 4-(4-oxo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carbonyl)-benzonitrile 
• 1386443-33-9 4-[hydroxy-(4-oxo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-methyl]-benzonitrile 
• 1194450-91-3 4-[(2,4,5,6-tetrahydro-4-oxo-1H-pyrrolo[3,2,1-ij]quinolin-8-yl)(1H-imidazol-1-yl)methyl]benzonitrile 
• 1386443-20-4 3-(4-oxo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carbonyl)-benzonitrile 
• 1386443-32-8 3-[hydroxy-(4-oxo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-methyl]benzonitrile 
• 1194451-04-1 3-[(2,4,5,6-tetrahydro-4-oxo-1H-pyrrolo[3,2,1-ij]quinolin-8-yl)(1H-imidazol-1-yl)methyl]benzonitrile 
• 1386443-19-1 8-(4-methoxybenzoyl)-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one 
• 1386443-31-7 8-[hydroxy-(4-methoxyphenyl)methyl]-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one 

Relevant articles and documents

Bismuth(iii)-catalyzed regioselective alkylation of tetrahydroquinolines and indolines towards the synthesis of bioactive core-biaryl oxindoles and CYP19 inhibitors

Bismuth(iii)-catalyzed regioselective functionalization at the C-6 position of tetrahydroquinolines and the C-5 position of indolines has been demonstrated. For the first time, one pot symmetrical and unsymmetrical arylation of isatins with tetrahydroquinolines was accomplished giving a completely new product skeleton in good to excellent yields. Most importantly, this protocol leads to the formation of a highly strained quaternary carbon stereogenic center, which is a challenging task. Benzhydryl and 1-phenylethyl trichloroacetimidates have been used as the alkylating partners to functionalize the C-6 and C-5 positions of tetrahydroquinolines and indolines, respectively. The scope of the developed methodology has been extended for the synthesis of the bioactive CYP19-inhibitor and its analogue.

Synthesis and Biological Evaluation of Fused Tricyclic Heterocycle Piperazine (Piperidine) Derivatives As Potential Multireceptor Atypical Antipsychotics

Herein, a novel series of multireceptor ligands was developed as polypharmacological antipsychotic agents using the designed multiple ligand approach between dopamine receptors and serotonin receptors. Among them, compound 47 possessed unique pharmacological features, exhibiting high affinities for D2, D3, 5-HT1A, 5-HT2A, and 5-HT6 receptors and low efficacy at the off-target receptors (5-HT2C, histamine H1, and adrenergic α1 receptor). Compound 47 showed dose-dependent inhibition of apomorphine- and MK-801-induced motor behavior, and the conditioned avoidance response with low cataleptic effect. Moreover, compound 47 resulted nonsignificantly serum prolactin levels and weight gain change compared with risperidone. Additionally, compound 47 possessed a favorable pharmacokinetic profile with oral bioavailability of 58.8% in rats. Furthermore, compound 47 displayed procognition properties in a novel object recognition task in rats. Taken together, compound 47 may constitute a novel class of atypical antipsychotic drugs for schizophrenia.

Novel imidazol-1-ylmethyl substituted 1,2,5,6-tetrahydropyrrolo[3,2,1-ij] quinolin-4-ones as potent and selective cyp11b1 inhibitors for the treatment of cushing's syndrome

CYP11B1 inhibition is a promising therapy for Cushing's syndrome. Starting from etomidate, references I and II, the title compounds were designed and synthesized. Cyclopropyl analogue 4 was identified as a CYP11B1 inhibitor more potent (IC50 = 2.2 nM) than leads and more selective (SF = 11) than I and metyrapone. Since it also showed potent inhibition of rat CYP11B1 and good selectivity over human CYP17 and CYP19, it is a promising candidate for further development.