13/02/2023 - Indole Building Blocks

Block, Arthur McB. et al. published their research in International Journal of Quantum Chemistry, Quantum Biology Symposium in 1975 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Synthetic Route of C10H8ClNO2

Structure-activity correlations for phenoxyacetic acids and indoleacetic acids used for plant growth regulation was written by Block, Arthur McB.;Clements, Richard G.. And the article was included in International Journal of Quantum Chemistry, Quantum Biology Symposium in 1975.Synthetic Route of C10H8ClNO2 This article mentions the following:

Calculations using self-consistent field (SCF) mol. orbital (MO) theory with complete neglect of differential overlap (CNDO) were carried out on a series of halo-substituted phenoxyacetic and indoleacetic acids. No net pos. charge development calculated for the N-H group in the substituted indoleacetic acids gave the observed order of auxin activity. No development of pos. charge in the 锜?pz system calculated for N was in any way comparable to the observed auxin activity increase. However, the energies of the lowest unoccupied mol. orbitals (LUMO) decreased nearly linearly with increasing auxin activity. Twelve substituted phenoxyacetic acids, also studied, showed a correlation between the LUMO energies and the square of the LUMO coefficients at the ortho position, resp., and plant auxin activity when the lipophilicity of mols. in the series was taken into account. The correlation coefficient of the activity as function of LUMO energy was virtually identical to that calculated from the data of Hansch and coworkers (1963), using ring substituent Hammett sigma values for the ortho position instead of the LUMO energies. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Synthetic Route of C10H8ClNO2).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from鑱紹acillus thuringiensis鑱絘nd鑱紹acillus velezensis鑱絘nd their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Moskalev, Nikolai et al. published their research in Tetrahedron in 2004 | CAS: 3484-23-9

2-Methyl-6-nitro-1H-indole (cas: 3484-23-9) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Safety of 2-Methyl-6-nitro-1H-indole

Synthesis of 4- and 6-substituted nitroindoles was written by Moskalev, Nikolai;Barbasiewicz, Michal;Makosza, Mieczyslaw. And the article was included in Tetrahedron in 2004.Safety of 2-Methyl-6-nitro-1H-indole This article mentions the following:

Enolizable ketones react with m-nitroaniline in the presence of strong base such as tert-BuOK to give 4- and 6-substituted nitroindoles. The reaction proceeds via oxidative nucleophilic substitution of hydrogen in m-nitroaniline with enolate anions in positions ortho to the amino group giving anionic 锜?sup>H adducts that are addnl. stabilized by intramol. interaction between the amino and the carbonyl group. Spontaneous oxidation of the 锜?sup>H adducts followed by the Bayer type condensation of the produced ortho-aminonitrobenzyl ketones gives 4- and 6-substituted nitroindoles. The scope of this reaction and its basic mechanistic features are discussed. In the experiment, the researchers used many compounds, for example, 2-Methyl-6-nitro-1H-indole (cas: 3484-23-9Safety of 2-Methyl-6-nitro-1H-indole).

Rani, S. Shobha et al. published their research in International Journal of Chemical Sciences in 2010 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). COA of Formula: C8H4N2O4

Antioxidant and DNA binding study of 2,2¹-(5,5′-methylenebis(1,3,4-oxadiazole-5,2-diyl)bis(sulfanyl)acetic acid bis(2-oxo-3-indolyl)hydrazides was written by Rani, S. Shobha;Agaiah, Bairi;Sarangapani, M.. And the article was included in International Journal of Chemical Sciences in 2010.COA of Formula: C8H4N2O4 This article mentions the following:

The synthesis of the target compounds was achieved by a reaction of 1H-indole-2,3-dione derivatives with hydrazine and chloroacetyl chloride, formation of 2-chloroacetic acid 2-(1,2-dihydro-2-oxo-3H-indol-3-ylidene)hydrazide derivatives, subsequent reaction with 5,5′-methylenebis[1,3,4-oxadiazole-2(3H)-thione] and the products thus obtained were confirmed by elemental anal., IR, NMR, MS. The title compounds were evaluated for their radical scavenging properties using a DPPH radical model [2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazinyl radical] and it was discovered that these compounds displayed antioxidant activity in comparison with ascorbic acid. The compounds were also evaluated in a herring sperm DNA model and it was discovered that these products displayed DNA binding properties in using cisplatin as a drug standard In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8COA of Formula: C8H4N2O4).

Shen, Minggui et al. published their research in Chemistry Letters in 2014 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Quality Control of 5,6-Difluoroindoline-2,3-dione

A simple and efficient procedure for the one-pot three-component synthesis of spiro[indoline-3,9′-tetrazolo[5,1-b]quinazoline]-2,8′(5’H)-dione in PEG-H₂O medium was written by Shen, Minggui;Wang, Juan;Shang, Shibin;Song, Zhanqian. And the article was included in Chemistry Letters in 2014.Quality Control of 5,6-Difluoroindoline-2,3-dione This article mentions the following:

Novel spiro[indoline-3,9′-tetrazolo[5,1-b]quinazoline]-2,8′(5’H)-dione derivatives I (R¹ = 5-F, 5-OCH₃, 7-F, etc; R² = H, CH₃, C₆H₅) were synthesized by the three-component reaction of isatins II (R² = H, CH₃, C₆H₅) 5-amino-1H-tetrazole and 5,5-dimethylcyclohexane-1,3-dione in PEG-H₂O medium catalyzed by p-TSA. This protocol provides a simple one-step procedure with the advantages of easy work-up, mild reaction conditions and environmental benignity were discussed. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Quality Control of 5,6-Difluoroindoline-2,3-dione).

Prey, V. et al. published their research in Monatshefte fuer Chemie in 1958 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Electric Literature of C14H11NO

1-Thiophthalide was written by Prey, V.;Kondler, P.. And the article was included in Monatshefte fuer Chemie in 1958.Electric Literature of C14H11NO This article mentions the following:

Treatment of 1-thiophthalide (I) with PhNH₂ at 190鎺?in a bomb tube resulted in a rearrangement to 2-thiophthalide (II). The mechanism of the rearrangement is discussed. Phthalide (6.7 g.) and 11.1 g. P₂S₅ in xylene refluxed 1 hr., the mixture filtered hot, the filtrate steam distilled, the residue cooled, the oily product filtered off, pressed, and recrystallized twice from absolute EtOH gave 4.5 g. I, m. 108-9鎺? mol. weight 148.6. Proof of structure was supported by hydrolysis of I to phthalide, m. 73鎺? detection of the CS group by treatment of I with 0.5N alc. KOH and several drops of 30% H₂O₂, warming, cooling, acidifying, and adding BaCl₂ to obtain BaSO₄, and detection of the CS group by Grote’s test (C.A. 25, 5876). I treated with HgCl₂ 1 in Et₂O 15 parts gave I-Hg Cl₂ adduct (III), decompose 185鎺? III treated with saturated aqueous KI decomposed with the formation of HgS. I (2.0 g.) and 5.0 g. freshly distilled PhNH₂ refluxed 5 hrs. at 185鎺? cooled, the precipitate filtered off, and washed with dilute HCl and dried gave 1.02 g. N-phenylphthalimidine (IV), m. 165鎺? from the filtrate was obtained 0.7 g. addnl. IV. I (2.0 g.) and 5.0 g. PhNH₂ heated 3 hrs. at 190鎺?in a bomb tube, the mixture treated with dilute HCl, the oily precipitate dried in vacuo, taken up in EtOH, filtered, EtOH removed from the filtrate, and the product recrystallized from tetrahydrofuran with C and then from H₂O gave 1.65 g. II, white needles, m. 57-8鎺? I and PhNH₂ heated 3 hrs. at 240鎺?in a bomb tube gave 94% IV, m. 164鎺? II (2.0 g.) and 5.0 g. PhNH₂ refluxed 12 hrs. at 185鎺? cooled, the mixture treated with 50 cc. 20% HCl, and the resulting precipitate crystallized from EtOH gave 1.8 g. unchanged II, m. 57-8鎺? II (2 g.) and 5.0 g. PhNH₂ heated 3 hrs. at 190鎺?gave 95% unchanged II, but this mixture heated 3 hrs. at 240鎺?gave 2.45 g. IV, m. 164-5鎺? IV (2.0 g.) and 5.0 g. PhNH₂ contained in a bomb tube treated with dry H₂S with cooling at -78鎺? the tube sealed, and heated 3 hrs. at 190鎺?gave only unchanged IV. A similar result was obtained by heating at 240鎺? I (2.0 g.) and 5.8 g. PhNHMe refluxed 4.5 hrs. gave only 1.8 g. unchanged I. A similar result was obtained by heating 3 hrs. at 190鎺? Similar unsuccessful results were obtained using I and PhNMe, I being recovered. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Electric Literature of C14H11NO).

Najafi, Meysam et al. published their research in Monatshefte fuer Chemie in 2014 | CAS: 320734-35-8

7-Bromooxindole (cas: 320734-35-8) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Computed Properties of C8H6BrNO

On the antioxidant activity of ortho- and meta-substituted indolin-2-one derivatives was written by Najafi, Meysam. And the article was included in Monatshefte fuer Chemie in 2014.Computed Properties of C8H6BrNO This article mentions the following:

The antioxidant activity of ortho- and meta-substituted indolin-2-one derivatives was investigated in the gas phase and water. The reaction enthalpies of the individual steps of three antioxidant mechanisms of the studied derivatives were calculated and compared with the corresponding values of indolin-2-one. The results show that electron-withdrawing substituents increase the bond dissociation enthalpy and ionization potential, whereas electron-donating substituents increase the proton affinity. The indolin-2-one derivatives with the lowest bond dissociation enthalpy, ionization potential, and proton affinity values were identified as the compounds with high antioxidant activity. The results show that indolin-2-one derivatives with substituents in the ortho position are promising potential novel antioxidants. The results also show that the protective role of indolin-2-one derivatives occurs via hydrogen atom transfer and a sequential proton loss electron transfer mechanism in the gas phase and water, resp. The calculated reaction enthalpies of the substituted indolin-2-ones are linearly dependent on the Hammett constants and E_HOMO such that the latter can be utilized in the selection of suitable substituents for the synthesis of novel antioxidants based on indolin-2-one. In the experiment, the researchers used many compounds, for example, 7-Bromooxindole (cas: 320734-35-8Computed Properties of C8H6BrNO).

Cele, Zamani E. D. et al. published their research in European Journal of Organic Chemistry in 2015 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Product Details of 14204-27-4

Applied Enantioselective Aminocatalysis: 浼?Heteroatom Functionalization Reactions on the Carbapenem (灏?Lactam Antibiotic) Core was written by Cele, Zamani E. D.;Arvidsson, Per I.;Kruger, Hendrik G.;Govender, Thavendran;Naicker, Tricia. And the article was included in European Journal of Organic Chemistry in 2015.Product Details of 14204-27-4 This article mentions the following:

The carbapenem (灏?lactam antibiotic) scaffold serves as a useful nucleophile in organocatalytic diarylprolinol trimethylsilyl ether mediated 浼?heterofunctionalization reactions leading to the formation of diverse products that bear multiple stereocenters in high diastereoselectivity and moderate to good yields. Under optimized conditions the synthesis of the target compounds was achieved using (2S)-2-[diphenyl[(trimethylsilyl)oxy]methyl]pyrrolidine (chiral prolinol-silyl ether) as a catalyst. Starting materials included (5R,6S)-6-[(1R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (4-nitrophenyl)methyl ester, 1,2-diazenedicarboxylic acid, 1,2-bis(1,1-dimethylethyl) ester, N-(hydroxy)carbamic acid ester, (nitros)benzene,2-(phenylthio)-1H-isoindole-1,3(2H)-dione, 2-(phenylseleno)-1H-i-Isoindole-1,3(2H)-dione. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Product Details of 14204-27-4).

Marasek-Ciolakowska, Agnieszka et al. published their research in International Journal of Molecular Sciences in 2020 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid

Formation of the secondary abscission zone induced by the interaction of methyl jasmonate and auxin in Bryophyllum calycinum: relevance to auxin status and histology was written by Marasek-Ciolakowska, Agnieszka;Saniewski, Marian;Dziurka, Michal;Kowalska, Urszula;Goraj-Koniarska, Justyna;Ueda, Junichi;Miyamoto, Kensuke. And the article was included in International Journal of Molecular Sciences in 2020.Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid This article mentions the following:

The interaction of Me jasmonate (JA-Me) and indole-3-acetic acid (IAA) to induce the formation of the secondary abscission zone in the middle of internode segments of Bryophyllum calycinum was investigated in relation to auxin status and histol. When IAA at 0.1% (weight/weight, in lanolin) was applied to the segments, the formation of the secondary abscission zone at a few mm above the treatment in the apical direction was observed On the contrary, IAA at 0.5% (weight/weight, in lanolin) did not induce the formation of the secondary abscission zone. JA-Me at 0.5% (weight/weight, in lanolin) applied to the middle of internode segments kept in the normal (natural) or inverted positions also induced the formation of the secondary abscission zone below and above parts of the treatment. Comprehensive analyses of plant hormones revealed that the balance of the endogenous levels of IAA in both sides adjacent to the abscission zone was significantly disturbed when the secondary abscission formation was induced by the application of IAA. These results strongly suggest that an auxin gradient is important in the formation of the secondary abscission zone in the internode segments of B. calycinum, and IAA gradient results from polar IAA transport from the application site. Further possible mechanisms of the formation of the secondary abscission zone in the internode segments of B. calycinum are also discussed in the interaction of JA-Me and IAA. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid).

Smith, Keith et al. published their research in Synthesis in 2003 | CAS: 150560-58-0

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Name: 5-Isopropylindoline-2,3-dione

Carbonylation of doubly lithiated N’-aryl-N,N-dimethylureas: A novel approach to isatins via intramolecular trapping of acyllithiums was written by Smith, Keith;El-Hiti, Gamal A.;Hawes, Anthony C.. And the article was included in Synthesis in 2003.Name: 5-Isopropylindoline-2,3-dione This article mentions the following:

Lithiation of N’-(2-bromoaryl)-N,N-dimethylureas with methyllithium and tert-butyllithium under nitrogen in anhydrous THF at 0 鎺矯 gave doubly lithiated arylurea derivatives, which react with carbon monoxide at 0 鎺矯 to give isatins in good yields. The scope of the reaction has been demonstrated by application to the synthesis of isatin itself and four substituted isatins bearing alkyl, chloro or fluoro groups. Double lithiation and quenching with ammonium chloride of N‘-(2-bromophenyl)-N,N-dimethylurea gave N‘-(2-bromophenyl)-N,N-dimethylurea. Lithiation of N‘-(2-bromophenyl)-N,N-dimethylurea with methyllithium was followed by addition of (1,1-dimethylethyl)lithium, effecting an bromine-lithium exchange. Sequential carbonylation with carbon monoxide and quenching gave 1H-indole-2,3-dione (isatin). In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Name: 5-Isopropylindoline-2,3-dione).

Mino, Takashi et al. published their research in Organic & Biomolecular Chemistry in 2019 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Quality Control of 6-Nitro-1H-indole

Synthesis and application of P,olefin type axially chiral ligands with sec-alkyl groups was written by Mino, Takashi;Yamaguchi, Daiki;Masuda, Chihiro;Youda, Junpei;Ebisawa, Toshibumi;Yoshida, Yasushi;Sakamoto, Masami. And the article was included in Organic & Biomolecular Chemistry in 2019.Quality Control of 6-Nitro-1H-indole This article mentions the following:

We synthesized N-trans-cinnamyl-N-cyclohexylaniline type aminophosphine 2 and a series of N-2-adamantyl-N-trans-cinnamylaniline type aminophosphines 3. Although aminophosphine 2 failed to find the existence of axial chirality, aminophosphines 3, which exist in the axial chirality in a C(aryl)-N(amine) bond by chiral HPLC anal. as 1-adamantyl type chiral ligands 1. Enantiomeric isomers of 3b, 3c, and 3d were obtained in an enantiomerically pure form. We also identified the palladium-catalyzed asym. allylic substitution of 1,3-diphenyl-2-propenyl acetate with indoles using aminophosphines 3b–d as effective chiral ligands in high enantioselectivities (up to 96% ee). In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Quality Control of 6-Nitro-1H-indole).