7384-07-8

Usage

Uses

Used in Pharmaceutical Industry:
3-Hydroxycarbazole is used as a pharmaceutical compound for its mutagenic properties. It is utilized in the development of drugs that target genetic mutations, potentially leading to novel treatments for various diseases and conditions.
Used in Chemical Research:
As a chemical compound with unique properties, 3-Hydroxycarbazole is used as a research material in the field of chemistry. It can be employed in the study of mutagenesis, chemical reactions, and the development of new chemical compounds with potential applications in various industries.
Used in Environmental Studies:
Due to its mutagenic properties, 3-Hydroxycarbazole can be used in environmental studies to assess the impact of pollutants and other environmental factors on the genetic material of living organisms. This can help in understanding the long-term effects of environmental exposure and contribute to the development of strategies for environmental protection and remediation.

InChI:InChI=1/C12H9NO/c14-8-5-6-12-10(7-8)9-3-1-2-4-11(9)13-12/h1-7,13-14H

Upstream product

• 18992-85-3 3-methoxycarbazole 
• 1592-95-6 3-bromo-9H-carbazole 
• 13314-76-6 1,2,3,4-tetrahydro-6-hydroxycarbazole 
• 246175-67-7 3-ethoxy-carbazole 
• 91569-08-3 2'-Amino-biphenyl-2,5-diol 
• 105946-79-0 2'-nitro-[1,1'-biphenyl]-2,5-dione 
• 103863-19-0 2'-Nitro-biphenyl-2,5-diol 
• 3449-49-8 6-methoxy-2,3,4,9-tetrahydro-1H-carbazol-1-one 
• 77120-61-7 hydroxy-6 dihydro-3,4 carbazole(2H)one-1 
• 104-94-9 4-methoxy-aniline 
• 104917-94-4 9-methyl-3H-pyrrolo<1,2-a>indol-3-one 
• 1208-86-2 N-(4-methoxyphenyl)phenylamine 
• 100717-42-8 6-ethoxy-1,2,3,4-tetrahydro-carbazole 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 

Relevant academic research and scientific papers

Diels-Alder reactions of 2- and 3-nitroindoles. A simple hydroxycarbazole synthesis

A Diels-Alder reaction of 3- and 2-nitroindoles with Danishefsky's diene gives the expected 2- and 3-hydroxycarbazoles in very good to excellent yields (73-91%) and with apparent complete regioselectivity.

Axially and Helically Chiral Cationic Radical Bicarbazoles: SOMO-HOMO Level Inversion and Chirality Impact on the Stability of Mono- And Diradical Cations

We report persistent chiral organic mono- and diradical cations based on bicarbazole molecular design with an unprecedented stability dependence on the type of chirality, namely, axial versus helical. An unusual chemical stability was observed for sterically unprotected axial bicarbazole radical in comparison with monocarbazole and helical bicarbazole ones. Such results were experimentally and theoretically investigated, revealing an inversion in energy of the singly occupied molecular orbital (SOMO) and the highest (doubly) occupied molecular orbital (HOMO) in both axial and helical bicarbazole monoradicals along with a subtle difference of electronic coupling between the two carbazole units, which is modulated by their relative dihedral angle and related to the type of chirality. Such findings allowed us to explore in depth the SOMO-HOMO inversion (SHI) in chiral radical molecular systems and provide new insights regarding its impact on the stability of organic radicals. Finally, these specific electronic properties allowed us to prepare a persistent, intrinsically chiral, diradical which notably displayed near-infrared electronic circular dichroism responses up to 1100 nm and almost degenerate singlet-triplet ground states with weak antiferromagnetic interactions evaluated by magnetometry experiments.

TEMPO-mediated late stage photochemical hydroxylation of biaryl sulfonium salts

The late stage photochemical hydroxylation of biaryl sulfonium salts was enabled with a TEMPO derivative as a simple oxygen source, in metal free conditions. The scope and mechanism of this exceptionally simple synthetic method, which constructs important arylated phenols from aromatic C-H bonds, are herein discussed.

Luminescent Chiral Exciplexes with Sky-Blue and Green Circularly Polarized-Thermally Activated Delayed Fluorescence

Luminescent exciplexes based on a chiral electron donor and achiral acceptors are reported as a new approach to design circularly polarized (CP) and thermally activated delayed fluorescence (TADF) emitters. This strategy results in rather high CP luminesc

Cis-Dihydroxylation of Tricyclic Arenes and Heteroarenes Catalyzed by Toluene Dioxygenase: A Molecular Docking Study and Experimental Validation

Molecular docking studies of toluene dioxygenase led to the prediction that angular and lateral cis-dihydroxylation of tricyclic arene and heteroarene substrates could occur. Biotransformations of biphenylene, dibenzofuran, carbazole and dibenzothiophene, using Pseudomonas putida UV4 whole cells, expressing toluene dioxygenase, confirmed that both angular and lateral cis-dihydroxylation had occurred in the predicted regioselective and stereoselective manner. The toluene dioxygenase-catalysed (Pseudomonas putida UV4) biotransformation of dibenzofuran was optimized, to produce 1,2-dihydrodibenzofuran-1,2-diol as the major metabolite in excellent yield. 2-Hydroxydibenzofuran, resulting from dehydration of 1,2-dihydrodibenzofuran-1,2-diol, was also found to undergo cis- dihydroxylation to give a very minor cis-dihydrodiol metabolite. The enantiopurity (>98% ee) and (1R,2S) absolute configuration of the major dibenzofuran cis -dihydrodiol was rigorously established by catalytic hydrogenation and formation of methoxy(trifluoromethyl)phenylacetate derivatives and by X-ray crystallography of an epoxide derivative. Biotransformation of carbazole yielded anthranilic acid as the major metabolite and was consistent with angular cis-dihydroxylation. Synthesis of a cis- diol epoxide derivative showed that the main cis-dihydrodiol metabolite of dibenzofuran has potential in the chemoenzymatic synthesis of natural products. (Figure presented.).

Copper(II) catalyzed aromatization of tetrahydrocarbazole: An unprecedented protocol and its utility towards the synthesis of carbazole alkaloids

An efficient protocol for the aromatization of tetrahydrocarbazole is described by using catalytic copper(II) chloride dihydrate in DMSO. This newly established methodology has utilized towards the synthesis of naturally occurring carbazole alkaloids, namely 3-methylcarbazole, 3-formyl carbazole, glycozoline, glycozolicine and clauszoline-K. In addition, the protocol is generalized for the aromatization of N-substituted tetrahydrocarbazole, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline and 1,2,3,4-tetrahydro β-carboline to give the corresponding heteroaromatic compounds from very good to excellent yield. Moreover, this method has been proven to be tolerant to a broad range of functional groups with excellent yields.

Fused imidazole compounds with indoleamine 2,3-dioxygenase inhibition activity

The invention relates to fused imidazole compounds, and a preparation method and application thereof. The structure of the compounds is shown in a general formula I, wherein the definitions of each group are as described in the specification. The compounds are capable of selectively inhibiting indoleamine 2,3-dioxygenase (IDO). The compounds provided by the invention can be used as IDO inhibitorsfor the treatment and/or prevention of diseases with the pathological characteristics of IDO mediated tryptophan metabolism pathways, such as cancer, eye diseases, autoimmune diseases, psychological disorders, depression, anxiety and other diseases.

Antioxidant effects of the hydroxy groups in the simple phenolic carbazoles

Antioxidant activities of the simple phenolic carbazoles 5-11 were evaluated by 2,2-diphenyl-1-picrylhydrazyl and 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulfonate)+ radical scavenging assays. The simple phenolic carbazoles 5-7, 9, and 11 exhibited stronger antioxidant activities than α-tocopherol, and similar antioxidant activities as phenolic carbazole alkaloids carazostatin (1), and carbazomadurins A (3) and B (4). Bond dissociation energies and highest occupied molecule orbital energy levels of a series of phenolic carbazoles including phenolic carbazole alkaloids were calculated. The reducing ability of the phenolic carbazole core could be important role for the antioxidant activity of carbazole alkaloids 1, 3, and 4.

Vascular barrier protective effects of 3-N- or 3-O-cinnamoyl carbazole derivatives

In this Letter, we investigated the barrier protective effects of 3-N-(MeO)n-cinnamoyl carbazoles (BS 1; n = 1, BS 2; n = 2, BS 3; n = 3) and 3-O-(MeO)3-cinnamoyl carbazole (BS 4) against high-mobility group box 1 (HMGB1)-mediated vascular disruptive responses in human umbilical vein endothelial cells (HUVECs) and in mice for the first time. Data showed that BS 2, BS 3, and BS 4, but not BS 1, inhibited HMGB1-mediated vascular disruptive responses and transendothelial migration of human neutrophils to HUVECs. BS 2, BS3, and BS 4 also suppressed HMGB1-induced hyperpermeability and leukocyte migration in mice. Interestingly, the barrier protective effects of BS 3 and BS 4 were better than those of BS 2. These results suggest that the number of methoxy groups substituted on the cinnamamide or cinnamate moiety of the 9H-3-carbazole derivative is an important pharmacophore for the barrier protective effects of these compounds.

A thermal cascade route to pyrroloisoindolone and pyrroloimidazolones

(Chemical Equation Presented) Flash vacuum pyrolysis (FVP) of indol-1-ylacrylate derivatives 11 and 15 or the isomeric indol-3-ylacrylates 21, 22, and 24 at 925°C (0.05 Torr) provides pyrrolo[1,2-a]indol-3-ones 2, 18, 28, and 29 in 53-90% yield by a cascade mechanism that involves a sigmatropic migration, elimination, electrocyclization sequence. Pyrrolo[1,2-a]imidazol-5- ones 3 and pyrrolo[1,2-c]imidazol-5-ones 4 were similarly obtained by FVP of corresponding 2,5-unsubstituted imidazol-1-ylacrylates (e.g., 33), with the former isomer predominating in ca. 80:20 ratio. Migration to the 2-position is therefore favored in the initial sigmatropic shift. FVP of 2-substituted imidazol-1-ylacrylates 35, 37, and 51 (825-875°C) instead give pyrrolo[1,2-c]imidazol-5-ones 56-58 only (88-91%), and that of 4,5-disubstituted imidazol-1-ylacrylates 39 and 41 (825-850°C) provide pyrrolo[1,2-a] imidazol-5-ones 59 and 60 exclusively (93-95%), and thus the selectivity of the initial shift can be controlled by the presence of substituents on the imidazole 2- and 5-positions. FVP of the benzimidazole analogues 61 and 62 at 950°C gave the pyrrolo[1,2-a]benzimidazol-1-ones 6 (71%) and 63 (36%), respectively.