27385-45-1

Usage

Uses

Used in Organic Chemistry:
1,3-Cyclohexanedione, mono(phenylhydrazone) is used as a reagent for the detection and determination of aldehydes and ketones. It forms yellow or orange colored complexes with aldehydes and ketones, making it useful for qualitative analysis in chemical laboratories.
Used in Synthesis:
1,3-Cyclohexanedione, mono(phenylhydrazone) is used as a building block for the synthesis of various other organic compounds.

Upstream product

• 504-02-9 1,3-cylohexanedione 
• 100-63-0 phenylhydrazine 
• 7732-18-5 water 
• 142-04-1 aniline hydrochloride 
• 59-88-1 phenylhydrazine hydrochloride 

Downstream Products

• 15128-52-6 1,2,3,9-tetrahydro-4H-carbazol-4-one 
• 113502-44-6 2-phenyl-6,7-dihydro-2H-indazol-4(5H)-one 
• 27385-52-0 N-{[(4-methylphenyl)sulfonyl]oxy}-1,2,3,9-tetrahydro-4H-carbazol-4-imine 
• 4828-96-0 cis-2,3,4,4a,9,9a-hexahydro-1H-carbazole 
• 27387-31-1 9-methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one 
• 102754-93-8 4-oxo-1,2,3,4-tetrahydrocarbazole phenylhydrazone 
• 886434-61-3 9-(4-fluorobenzyl)-1,2,3,9-tetrahydrocarbazol-4-one 

Relevant academic research and scientific papers

New azepino[4,3-b]indole derivatives as nanomolar selective inhibitors of human butyrylcholinesterase showing protective effects?against NMDA-induced neurotoxicity

Several 6-substituted 3,4,5,6-tetrahydroazepino[4,3-b]indol-1(2H)-one (THAI) derivatives were synthesized and evaluated for their activity as cholinesterase (ChE) inhibitors. The most potent inhibitors were identified among 6-(2-phenylethyl)-THAI derivatives, and in particular compounds 12b and 12d proved to be very active against human BChE (IC50?=?13 and 1.8?nM, respectively), with 1000-fold selectivity over AChE. Structure-activity relationships highlighted critical features (e.g., ring fusion [4,3-b], integrity of the lactam CONH function) and favorable physicochemical properties of the 6-(2-phenylethyl) group (i.e., optimal position, size and lipophilicity of phenyl substituents). The effects of a number of compounds against NMDA-induced SH-SY5Y neuronal cell injury were also evaluated. Treatment with 12b increased cell viability in SH-SY5Y cells pretreated with 250?μM NMDA, with significant effects (P??0.05) at concentrations between 0.5 and 5?μM. These findings suggest that THAI can be used as a scaffold for developing new drug leads for the treatment of Alzheimer-type neurodegeneration syndrome.

An expedient synthesis of regioisomeric pyrazole-fused cycloalkanones

Described herein is a novel one-pot procedure for the synthesis of pyrazoles through the in situ generation of a monohydrazone of cyclic 1,3-diones and subsequent cyclization with N,N-dimethylformamide dimethyl acetal. This route provides pyrazoles that have limited accessibility by other methods. Georg Thieme Verlag Stuttgart.

Conformationally restrained carbazolone-containing α,γ-diketo acids as inhibitors of HIV integrase

Since α,γ-diketo acid (DKA) compounds were identified as potent and selective inhibitors for HIV integrase, numerous structural modification studies have been carried out to search for a clinical candidate as a supplement for the highly active antiretroviral therapy regimen. Due to the lack of structural information on inhibitor-integrase interactions, a comprehensive structure-activity relationship study is necessary. Most of the reported modification studies on the key α,γ-diketo acid pharmacophore focused on substituting the carboxylate moiety with its bioisosteres or other electron-pair bearing heterocycles. We were interested in studying the conformation and geometry of the central diketo moiety. A series of carbazolone-containing α,γ-diketo acids were designed and synthesized by applying conformational restraint onto the open-chain form of the diketo acid. These compounds showed anti-integrase activity in the low micromolar range, and integrase assay results indicated that the geometry of the diketo acid moiety is crucial to potency. Carbazol-1-one containing DKA analogs (7-8) showed a 2- to 3-fold increase in activity compared with those of carbazol-4-one containing DKA analogs (5 and 6). Alkylation of carbazol-4-one DKA nitrogen (6a-c) led to a loss of activity, suggesting this nitrogen atom may directly interact with the active site of integrase. The halogens (7b-d) and para-fluorobenzyl substituents (8a-d) on carbazol-1-one ring had little effect on potency.

Synthesis of β3 adrenergic receptor agonist LY377604 and its metabolite 4-hydroxycarbazole, labeled with carbon-14 and deuterium

Synthesis of 14C-radiolabeled 4-hydroxycarbazole was accomplished starting from aniline-[U-14C], based on zinc chloride initiated Fischer cyclization of the phenylhydrazone prepared from phenylhydrazine-[U-14C] and cyclohexane-1,3-dione. The resulting tetrahydrooxocarbazole was subjected to dehydrogenation-aromatization using palladium on carbon. The aromatized 4-hydroxycarbazole-[4b,5,6,7,8,8a- 14C] was then used for the synthesis of 14C-labeled β3 adrenergic receptor agonist LY377604. The introduction of four deuteria in the carbazole fragment of LY377604 accomplished by its initial bromination and subsequent catalytic deuteration of the resulting tetrabromide. A similar approach was used for the conversion of 4-hydroxycarbazole into its tetradeutero-isotopomer. Copyright

Novel substituted 4-aminomethylpiperidines as potent and selective human β3-agonists. Part 1: Aryloxypropanolaminomethylpiperidines

The synthesis and SAR of a series of human β3 adrenoreceptor agonists based on a template derived from a common pharmacophore coupled with 4-aminomethylpiperidine is described. Potent and selective agents were identified such as 26 that was in vitro active in CHO cells expressing human β3-AR (EC50=49 nM, IA=1.1), and in vivo active in a transgenic mouse model.

Molecular yardsticks. Rigid probes to define the spatial dimensions of the benzodiazepine receptor binding site

A series of rigid planar azadiindoles (8a, 8b, and 8d), benzannelated pyridodiindoles (11a, 11b, and 11d), and indolopyridoimidazoles (11c, 20, and 24) were synthesized from 4-oxo-1,2,3,4-tetrahydro-β-carboline 5 via the Fischer indole cyclization with the appropriate arylhydrazines. These analogues were employed as probes ('molecular yardsticks') to define the spatial dimensions of the lipophilic regions of the benzodiazepine receptor (BzR) binding cleft. Benzannelated indoles 11a-d and indolopyridoimidazoles 20 and 24 were important in establishing an area of negative interaction (S1, see Figure 6, part b) in the binding cleft common to the interactions of both inverse agonists and agonists. Data from this chemical and computer- assisted analysis of the pharmacophore (see Figure 6) indicates that inverse agonists and agonists bind to the same binding region, but the pharmacophoric descriptors required for the two activities are different, in keeping with previous studies with these planar ligands. However, the hydrogen bond donating site H1 and the lipophilic region L1 in the receptor binding site are common interactions experienced by both series of ligands. The low affinities of both indolo[3,2-c]carbazole (3a) and indolo[3,2-b]isoquinoline (3b) for the BzR are consonant with the requirements of a hydrogen bond acceptor interaction at donor site H1 and a hydrogen bond donor interaction at acceptor site A2 for potent inverse agonist activity in the β-carboline series. The hydrochloride salts of 1-aza- 8a (IC50 10.6 nM), 2-aza- 8b (IC50 51.5 nM), and 4-azadiindole 8d (IC50 11.2 nM) were found to be much more soluble in water than the corresponding salt of the parent diindole 2. Moreover, aza analogues 8a and 8b were shown to be partial inverse agonists with proconvulsant potencies comparable to that of the parent diindole 2.

Process for the preparation of 4-hydroxycarbazole

The present invention provides a process for the preparation of 4-hydroxycarbazole by the dehydration of 1,2,3,4-tetrahydro-4-oxocarbazole, wherein the reaction is carried out in aqueous alkaline solution, using Raney nickel as catalyst.