Category: indole-building-block

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

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

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

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

Synthesis, molecular docking and enzyme inhibitory approaches of some new chalcone-engrafted pyrazoles as potential antialzheimer, antidiabetic and antioxidant agents was written by Islam, Mohammad Shahidul;Al-Majid, Abdullah Mohammed;Sholkamy, Essam Nageh;Yousuf, Sammer;Ayaz, Muhammad;Nawaz, Asif;Wadood, Abdul;Rehman, Ashfaq Ur;Verma, Ved Prakash;Bari, Ahmed;Haukka, Matti;Soliman, Saied M.;Barakat, Assem. And the article was included in Journal of Molecular Structure in 2022.SDS of cas: 827-01-0 This article mentions the following:

A series of pyrazole-based chalcones I (R = Ph, 3-MeC₆H₄, 2-benzothienyl, 3-indolyl, 5-chloro-3-methyl-1-phenylpyrazol-4-yl, etc.) was designed and constructed in two steps from readily available acetylacetone, phenylhydrazine and DMF-DMA as starting materials. The synthesized chalcone analogs were screened for in vitro anti-acetylcholinesterase potential, antidiabetic potential against 伪-glucosidase and 伪-amylase, and antioxidant potentials against DPPH free radicals. The compounds I (R = ferrocenyl, Ph, 1-naphthyl, 3-BrC₆H₄, 3-O₂NC₆H₄) showed strongest acetylcholine esterase inhibition (AChEI) with IC₅₀ values of 5 卤 1.16渭g/mL, 8 卤 0.14渭g/mL, 8 卤 0.57渭g/mL, 10 卤 1.73渭g/mL and 10 卤 0.60渭g/mL, resp. The highest inhibition against 伪-glucosidase was demonstrated by compounds I (R = 4-ClC₆H₄, 3-O₂NC₆H₄, 3-FC₆H₄, 4-MeOC₆H₄, 3-MeC₆H₄, Ph) with IC₅₀ values of 4 卤 0.14, 6 卤 0.43, 8 卤 0.43, 10 卤 0.11, 11 卤 0.28 and 12 卤 0.57渭g/mL, resp., whereas, the compounds I (R = 5-bromo-3-indolyl, benzothiophen-2-yl, 1-methyl-3-indolyl, 5-chloro-3-indolyl, 5-chloro-3-methyl-1-phenylpyrazol-4-yl) showed prominent 伪-amylase inhibition with IC₅₀ values of 20 卤 1.15渭g/mL, 30 卤 0.60渭g/mL, 40 卤 0.72渭g/mL, 40 卤 0.50渭g/mL, and 60 卤 2.19渭g/mL, resp.. The highest anti-oxidant potential against DPPH free radicals was demonstrated by compounds I (R = 1-methyl-3-indolyl, 3-indolyl, 5-chloro-3-indolyl) with IC₅₀ values of 160 卤 5.77, 260 卤 4.63, and 360 卤 4.04渭g/mL, resp. Mol. docking was used to study their interaction with the active site of enzymes. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0SDS of cas: 827-01-0).

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. 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). SDS of cas: 827-01-0

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

Simple syntheses of 5-fluoro/ chloro/ bromoindole-2-methanols and 5-fluoro/ chloro/ bromoindole-2-aldehydes was written by Narayana, B.;Ashalatha, B. V.;Raj, K. K. Vijaya. And the article was included in Organic Chemistry: An Indian Journal in 2006.Recommanded Product: Methyl 5-bromo-1H-indole-2-carboxylate This article mentions the following:

Efficient and simple methods for the syntheses of 5-haloindole-2-methanols and 5-haloindole-2-aldehydes have been described. 5-Haloindole-2-methanols were prepared by reduction of Me 5-haloindole-2-carboxylates with sodium borohydride in methanol/ THF media and 5-haloindole-2-aldehydes were prepared from the prepared 5-haloindole-2-methanols by oxidation with pyridinium chlorochromate or chromium trioxide-pyridine prepared in situ. The synthesized compounds were isolated in good yields and characterized by ¹H NMR, ¹³C NMR, FABMS and elemental anal. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Recommanded Product: Methyl 5-bromo-1H-indole-2-carboxylate).

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: Methyl 5-bromo-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

Sulfur-Directed C₇-Selective Alkenylation of Indoles under Rhodium Catalysis was written by Kona, Chandrababu Naidu;Nishii, Yuji;Miura, Masahiro. And the article was included in Organic Letters in 2021.SDS of cas: 14204-27-4 This article mentions the following:

In this report, a Rh-catalyzed C7-selective alkenylation of indole derivatives using a new sulfur directing group N-SCy is reported. A notable feature of this system is that the directing group is readily installed to the indoles and easily removed after the catalysis under mild conditions. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4SDS of cas: 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.SDS of cas: 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

Bromination of 2,3-dimethylindole was written by Kost, A. N.;Yudin, L. G.;Budylin, V. A.;Yaryshev, N. G.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1965.Product Details of 4583-55-5 This article mentions the following:

Bromination of 2,3-dimethylindole (I) in concentrated H₂SO₄ containing Ag₂SO₄ gave 75% 5-bromo-2,3-dimethyl-indole (II), m. 138掳. Bromination of 1-acetyl-2,3-dimethyl-indole followed by hydrolysis gave 70% 5-bromo-2,3-dimethyl-indole (III), b₁₀ 135-7掳, n²⁰_D 1.5923, d₂₀ 0.9982. Dehydration of III with chloranil gave 45% II. II was also prepared in 70% yield by acid treatment of 2-butanone p-bromophenylhydrazone. Bromination in acid of 2,3-dimethylindoline gave 50% 6-bromo-2,3-dimethylindoline (IV), b₄ 132-4掳. Dehydration of IV with chloranil gave 37% 6-bromo-2,3-dimethylindole (V), m. 164掳. II and V could also be distinguished by ir bands at 590 cm.^-1 in II and 1326 cm.^-1 in V. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Product Details 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. 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.Product Details 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

Pd(II)-Catalyzed oxidative dearomatization of indoles: substrate-controlled synthesis of indolines and indolones was written by Fang, Xinxin;Gao, Shang;Wu, Zijun;Yao, Hequan;Lin, Aijun. And the article was included in Organic Chemistry Frontiers in 2017.COA of Formula: C10H10BrN This article mentions the following:

A Pd(II)-catalyzed oxidative Wacker-type cyclization/dearomatization of 2,3-disubstituted indoles with mol. oxygen as the oxidant was developed. This strategy provided straightforward access to diverse fused indolines bearing C2-oxygenated quaternary stereocenters with good functional group tolerance and high atom economy. Meanwhile, a Pd(II)-catalyzed oxidation/dearomatization of 2-substituted indoles was presented, which enabled the facile synthesis of indolones. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5COA of Formula: C10H10BrN).

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. 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.COA of Formula: C10H10BrN

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