Indole Building Blocks

Selective halogen-lithium exchange in bromophenylalkyl halides was written by Parham, William E.;Jones, Lawrence D.;Sayed, Yousry A.. And the article was included in Journal of Organic Chemistry in 1976.Reference of 5388-42-1 This article mentions the following:

Exchange of the aryl halide atom in o-BrC6H4CH2Cl, o-BrC6H4(CH2)2Br, and o-BrC6H4(CH2)3Cl for Li was carried out with BuLi in THF-hexane at -100掳. The stable lithio derivatives reacted with a variety of electrophiles; e.g., o-LiC6H4CH2Cl (I) with H2O, cyclohexanone, or PhNCO at low temperature gave, resp., PhCH2Cl, II, and III. I with H2O at room temperature gave 9,10-dihydroanthracene (not benzocyclopropene). Benzocyclobutene was formed from o-LiC6H4(CH2)2Br under similar conditions. O-halobenzyl bromides were lithiated at the benzyl bromine atom and underwent subsequent coupling to bibenzyl. O-BrC6H4(CH2)3Br with BuLi underwent intramol. coupling to indan. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Reference of 5388-42-1

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

Ir-Catalyzed Reversible Acceptorless Dehydrogenation/Hydrogenation of N-Substituted and Unsubstituted Heterocycles Enabled by a Polymer-Cross-Linking Bisphosphine was written by Zhang, Deliang;Iwai, Tomohiro;Sawamura, Masaya. And the article was included in Organic Letters in 2020.Formula: C8H6N2O2 This article mentions the following:

In the presence of a catalyst generated from [Ir(cod)Cl]₂ and the crosslinked polystyrene-bound diphosphine PS-DPPBz, indolines and selected partially saturated five- and six-membered nitrogen heterocycles underwent reversible acceptorless dehydrogenation to give aromatic nitrogen heterocycles. The method was used for the dehydrogenation of N-substituted indolines with various nitrogen substituents and substituents with various electronic and steric effects. Under 40 atm. of H₂, indoles and a quinoline, isoquinoline, and quinoxaline underwent hydrogenation in the presence of the resin-bound iridium catalyst to yield partially saturated nitrogen heterocycles. A reaction pathway involving oxidative addition of an N-adjacent C(sp³)-H bond to a bisphosphine-coordinated Ir(I) center is proposed for the dehydrogenation of N-substituted substrates. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Formula: C8H6N2O2).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Formula: C8H6N2O2

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

Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells was written by Nishiyama, Takashi;Hatae, Noriyuki;Yoshimura, Teruki;Takaki, Sawa;Abe, Takumi;Ishikura, Minoru;Hibino, Satoshi;Choshi, Tominari. And the article was included in European Journal of Medicinal Chemistry in 2016.Quality Control of Methyl 5-fluoro-1H-indole-2-carboxylate This article mentions the following:

A convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O₂ atmosphere as an important step is reported. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions I (R¹ = R² = H, CH₃; R³ = H, 6-OCH₃, 5,6-(OCH₃)₂, 7-CH₃, 6-NO₂, etc.; R⁴ = H, MOM) have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Quality Control of Methyl 5-fluoro-1H-indole-2-carboxylate).

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Quality Control of Methyl 5-fluoro-1H-indole-2-carboxylate

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

Oxidative cleavage reaction of substituted indoles catalyzed by plant cell cultures was written by Takemoto, Masumi;Iwakiri, Yasutaka;Tanaka, Kiyoshi. And the article was included in Heterocycles in 2007.Application of 4583-55-5 This article mentions the following:

We have developed a novel method for the oxidative cleavage of indole carbon double bonds in the presence of H₂O₂ using plant cell cultures as peroxidase. The oxidative method has some advantage, as features such as mild reactions, good yields, easy work-up, and safety. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Application of 4583-55-5).

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Application of 4583-55-5

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

Synthesis and in-vitro anticancer activity of 3,5-bis(indolyl)-1,2,4-thiadiazoles was written by Kumar, Dalip;Kumar, N. Maruthi;Chang, Kuei-Hua;Gupta, Ritika;Shah, Kavita. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Computed Properties of C9H5BrN2 This article mentions the following:

A series of 3,5-bis(indolyl)-1,2,4-thiadiazoles were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. Indole-3-thiocarboxamides, e.g., I, reacted with iodobenzene diacetate via oxidative dimerization to give 3,5-bis(indolyl)-1,2,4-thiadiazoles, e.g., II. Among the synthesized bis(indolyl)-1,2,4-thiadiazoles, the compound II with 4-chlorobenzyl and methoxy substituents showed the most potent activity. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6Computed Properties of C9H5BrN2).

5-Bromo-3-cyanoindole (cas: 90271-86-6) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Computed Properties of C9H5BrN2

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

Co,N-Codoped Porous Carbon-Supported Co_yZnS with Superior Activity for Nitroarene Hydrogenation was written by Zhang, Guangji;Tang, Feiying;Wang, Xiaoying;An, Ping;Wang, Liqiang;Liu, You-Nian. And the article was included in ACS Sustainable Chemistry & Engineering in 2020.Synthetic Route of C8H6N2O2 This article mentions the following:

Preparation of chemoselective hydrogenation catalyst containing both CoNx and CoyZnS supported on N-doped porous carbon (CoN_x-Co_yZnS@NPC-Z) was reported. The CoN_x-Co_yZnS@NPC-Z catalyst were prepared by pyrolyzing the protein-metal-ion networks, followed by treatment with acid. The CoN_x-Co_yZnS@NPC-Z-3 catalyst delivered high catalytic activity and selectivity in chemoselective hydrogenation of nitroarenes afforded aryl amines R-NH₂ [R = Ph, 4-ClC₆H₄, 2-naphthyl, etc.] with almost full conversion and >98% selectivity in water/methanol mixture solvents at 90掳C under 5 bar of H₂ pressure for 3h of reaction. Also Schiff-base derivatives R¹CH=NR² [R¹ = Ph, 4-ClC₆H₄, 4-MeOC₆H₄, etc.; R² = Ph, 2-MeC₆H₄, 4-ClC₆H₄, etc.] were prepared via one-pot reductive amination of aryl aldehydes with aromatic nitro compounds using CoN_x-Co_yZnS@NPC-3 catalyst. Notably, the catalytic hydrogenation could work even under 1 bar of H₂ pressure and at room temperature with high conversion and selectivity. Besides, CoN_x-Co_yZnS@NPC-Z-3 exhibited remarkable tolerance to CO or H₂S poisoning and acid erosion. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Synthetic Route of C8H6N2O2).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. 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). Synthetic Route of C8H6N2O2

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

Consecutive C1-Homologation / Displacement Strategy for Converting Thiosulfonates into O,S-Oxothioacetals was written by Ielo, Laura;Pillari, Veronica;Miele, Margherita;Holzer, Wolfgang;Pace, Vittorio. And the article was included in Advanced Synthesis & Catalysis in 2020.HPLC of Formula: 14204-27-4 This article mentions the following:

A conceptually intuitive synthesis of oxothioacetals RSCH₂OR¹ [R = Me, Ph, 4-FC₆H₄, 2-F₃CC₆H₄, (4,6-dimethylpyrimidin-2-yl); R¹ = Me, 2-BrC₆H₄, 1-naphthyl, etc.] was reported starting from thiosulfonates as electrophilic sulfur donors. The installation of a reactive CH₂Cl motif with a homologating carbenoid reagent, followed by the immediate nucleophilic displacement with alc. groups [(hetero)-aromatic, aliphatic] offered a convenient access to the title compounds RSCH₂OR¹. Genuine chemoselectivity was uniformly observed in the case of multi-functionalized systems. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4HPLC of Formula: 14204-27-4).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.HPLC of Formula: 14204-27-4

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

Platinum(II)-catalyzed dehydrative C3-benzylation of electron-deficient indoles with benzyl alcohols was written by Hikawa, Hidemasa;Matsuura, Yuuki;Kikkawa, Shoko;Azumaya, Isao. And the article was included in Organic Chemistry Frontiers in 2019.Related Products of 4769-96-4 This article mentions the following:

A synthetic strategy for the water-promoted direct dehydrative coupling of indoles I (R = H, Me; R¹ = 6-NO₂, 7-COOH, 5-CN, etc.; R² = H, COOH, phenyl) with benzyl alcs. ArC(OH)(R³)(R⁴) (Ar = C₆H₅, 4-MeOC₆H₄, 3-F₃CC₆H₄, CH=CHC₆H₅, etc.; R³ = Ph, 4-chlorophenyl, Me, etc.; R⁴ = H, Ph) catalyzed by PtCl₂(PhCN)₂ in 1,2-dichloroethane has been developed. Water mols. significantly accelerate C-C bond formation to construct 3-benzylindoles II, whereas the reaction proceeds slowly under anhydrous conditions. Comparative rate plots for reactions in the presence of H₂O and D₂O show a kinetic solvent isotope effect (KSIE) of 1.5. A Hammett study of the dehydrative reaction of para-substituted benzhydrols shows neg. 蟻 values, indicating a build-up of cationic charge during the rate-determining sp³ C-O bond cleavage step. This catalytic system can be used on the gram scale with simplified product isolation and catalysis is performed using 1 mol% of a Pt(II) catalyst with an addnl. mol. of water. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Related Products of 4769-96-4).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Related Products of 4769-96-4

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

Design of Helicobacter pylori glutamate racemase inhibitors as selective antibacterial agents: A novel pro-drug approach to increase exposure was written by Basarab, Gregory S.;Hill, Pamela J.;Rastagar, Abdullah;Webborn, Peter J. H.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2008.Quality Control of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

High-throughput screening uncovered a pyrazolopyrimidinedione hit as a selective, low micromolar inhibitor of Helicobacter pylori glutamate racemase (MurI). Variation of the substituents around the scaffold led to low nanomolar inhibitors and improved antibacterial activity. The challenge in this program was to translate excellent enzyme inhibition into potent antibacterial activity and pharmacokinetics suitable for oral therapy. Compounds were profiled for MurI inhibition, activity against H. pylori, microsomal stability, and pharmacokinetics in mice. Iterative cycles of analog synthesis and biol. testing led to compounds with substituents optimized for both low MICs (鈮? 渭g/mL) and good microsomal stability. In order to achieve high bioavailability, a novel pro-drug approach was implemented wherein a solubilizing sulfoxide moiety is oxidized in vivo to a sulfone. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Quality Control of 5-Chloroindole-3-carboxaldehyde).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Quality Control of 5-Chloroindole-3-carboxaldehyde

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

Novel Cyanine Dyes with Vinylsulfone Group for Labeling Biomolecules was written by Park, Jin Woo;Kim, YoungSoo;Lee, Kee-Jung;Kim, Dong Jin. And the article was included in Bioconjugate Chemistry in 2012.Formula: C13H17NO3S This article mentions the following:

Novel vinylsulfone cyanine dyes (em. 550-850 nm) were designed and synthesized for fluorescent labeling of biomols. via 1,2-addition reaction in aqueous conditions. Due to the virtue of chem. structures of both fluorophore and reactive group, these dyes could be significantly stable and reactive in various aqueous/organic conditions. A wide variety of pH, temperature, buffer concentration, and protein were tested for the optimal labeling condition. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Formula: C13H17NO3S).

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Formula: C13H17NO3S

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