12/10/2022 - Page 7 of 8 - Indole Building Blocks

DeRatt, Lindsey G’s team published research in Organic Letters in 2019-12-06 | 399-76-8

Organic Letters published new progress about Heterocyclic compounds, nitrogen Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Product Details of C9H6FNO2.

DeRatt, Lindsey G.; Lawson, Edward C.; Wang, Chao-Yuan; Kuduk, Scott D. published the artcile< Mild Intramolecular Ring Opening of Oxetanes>, Product Details of C9H6FNO2, the main research area is oxetane carboxamide nucleophile intramol ring opening.

Herein, an intramol. ring opening of oxetane carboxamides with mild nucleophiles, such as nitrogen heterocycles, is presented. The reaction proceeds under metal-free basic conditions which is highly unusual in ring opening reactions of oxetanes. Amide formation and oxetane ring opening/cyclization in a one-pot approach affords high levels of mol. complexity in a single step from simple, readily available substrates.

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

Lu, Wen-Jun’s team published research in Acta Crystallographica, Section E: Structure Reports Online in 2012-01-31 | 23077-43-2

Acta Crystallographica, Section E: Structure Reports Online published new progress about Crystal structure. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Synthetic Route of 23077-43-2.

Lu, Wen-Jun; Zou, Zhi-Hong; Luo, Yang-Hui published the artcile< 5-Fluoro-1H-indole-3-carboxylic acid>, Synthetic Route of 23077-43-2, the main research area is crystal structure fluoroindolecarboxylic acid; mol structure fluoroindolecarboxylic acid; hydrogen bond fluoroindolecarboxylic acid; indolecarboxylic fluoro acid crystal mol structure.

In 5-fluoro-1H-indole-3-carboxylic acid, C9H6FNO2, the carboxyl group is twisted slightly away from the indole-ring plane [dihedral angle = 7.39(10)°]. In the crystal, carboxyl inversion dimers linked by pairs of O-H···O H bonds generate R22(8) loops and N-H···O H bonds connect the dimers into (101̅) sheets. Crystallog. data are given.

Zhang, Ting-Yu’s team published research in Organic Letters in 2018-01-05 | 23077-43-2

Organic Letters published new progress about Cyclization. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Formula: C9H6FNO2.

Zhang, Ting-Yu; Liu, Chang; Chen, Chao; Liu, Jian-Xin; Xiang, Heng-Ye; Jiang, Wei; Ding, Tong-Mei; Zhang, Shu-Yu published the artcile< Copper-Mediated Cascade C-H/N-H Annulation of Indolocarboxamides with Arynes: Construction of Tetracyclic Indoloquinoline Alkaloids>, Formula: C9H6FNO2, the main research area is tetracyclic indoloquinoline alkaloid preparation cascade annulation.

An efficient and environmentally benign Cu-mediated method was developed for direct cascade C-H/N-H annulation to construct polyheterocyclic indoloquinoline scaffolds (e.g. I). This method highlights an emerging strategy for transforming inert C-H bonds into versatile functional groups in organic synthesis and provides a new versatile approach for the efficient synthesis of indolo[3,2-c] and [2,3-c]quinoline alkaloids.

Organic Letters published new progress about Cyclization. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Formula: C9H6FNO2.

Banerjee, Sovan Lal’s team published research in Journal of Colloid and Interface Science in 2021-05-31 | 950846-89-6

Journal of Colloid and Interface Science published new progress about Antifouling agents. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Application In Synthesis of 950846-89-6.

Banerjee, Sovan Lal; Saha, Pabitra; Ganguly, Ritabrata; Bhattacharya, Koushik; Kalita, Uddhab; Pich, Andrij; Singha, Nikhil K. published the artcile< A dual thermoresponsive and antifouling zwitterionic microgel with pH triggered fluorescent ""on-off"" core>, Application In Synthesis of 950846-89-6, the main research area is thermoresponsive antifouling zwitterionic microgel fluorescence; Antifouling; Dual thermoresponsiveness; Fluorescence; LSCT; Microgel; UCST; Zwitterion.

A unique, tailor-made, zwitterionic, dual thermoresponsive and fluorescent microgel probe was synthesized via Reversible Addition Fragmentation chain-Transfer (RAFT) polymerization Microgels were prepared via oil in water (o/w) emulsion polymerization where poly(carboxybetaine) (PCB) acted as a macro-RAFT reagent as well as an emulsifier. The presence of poly(N-vinylcaprolactam) (PNVCL) in the microgel system imparts the thermoresponsiveness to the system and the presence of a rhodamine derivative as fluorophore makes it responsive to pH change of the system by showing a fluorescence emission at 580 nm (reddish orange color). The dual thermoresponsiveness [i.e. the presence of upper critical solution temperature (UCST @ 12°C) as well as lower critical solution temperature (LCST @ 33°C)] of the microgels was studied via UV-visible spectroscopy (UV-vis) and temperature responsive dynamic light scattering (DLS) analyses. Presence of the PCB in the corona-crosslinked microgel, played a vital role in the formation of self-assembled structure as well as in protein immobilization (antifouling activity). Antifouling property was studied using UV-vis spectroscopy where bovine serum albumin (BSA) was taken as a model protein. The presence of the pH-responsive fluorescence, thermoresponsiveness as well as antifouling properties makes this zwitterionic microgel system a potential a potential candidate for medical diagnostics and for drug delivery vehicles.

Luise, Nicola’s team published research in European Journal of Organic Chemistry in 2019 | 93247-78-0

European Journal of Organic Chemistry published new progress about Bicyclic compounds Role: SPN (Synthetic Preparation), PREP (Preparation). 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, SDS of cas: 93247-78-0.

Luise, Nicola; Wyatt, Eleanor W.; Tarver, Gary J.; Wyatt, Paul G. published the artcile< A Continuous Flow Strategy for the Facile Synthesis and Elaboration of Semi-Saturated Heterobicyclic Fragments>, SDS of cas: 93247-78-0, the main research area is semisatd heterobicycle preparation hydrogenation.

An efficient hydrogenation protocol under continuous flow conditions was developed for the synthesis of underrepresented semi-saturated bicyclic fragments containing highly sp3-rich skeletons for fragment-based drug discovery (FBDD) programs. Excellent yields were generally achieved by using Pd/C (10% weight/weight) and RaNi at 25-150° under 4-100 bar of hydrogen pressure. The generated fragments, with appropriate physicochem. properties, present diverse hydrogen-bonding pharmacophores and useful vectors for their synthetic elaboration in the optimization stage. Successive, simple functionalizations in continuous flow were accomplished to demonstrate the opportunity to develop multi-step continuous flow synthesis of valuable starting points for FBDD campaigns. A conclusive quality control (QC) was essential to discard those structures which do not fit the typical fragment library parameters.

Xu, Hui’s team published research in Bioorganic & Medicinal Chemistry Letters in 2010-12-15 | 4771-48-6

Bioorganic & Medicinal Chemistry Letters published new progress about Fungicides. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Product Details of C10H9NO.

Xu, Hui; Wang, Yang-Yang published the artcile< Antifungal agents. Part 5: Synthesis and antifungal activities of aminoguanidine derivatives of N-arylsulfonyl-3-acylindoles>, Product Details of C10H9NO, the main research area is arylsulfonylacylindole aminoguanidine preparation antifungal structure activity relationship.

In order to discover more promising antifungal agents, a series of aminoguanidine derivatives of N-arylsulfonyl-3-acylindoles were prepared and evaluated in vitro for their antifungal activities against seven phytopathogenic fungi. Some of the compounds exhibited more potent antifungal activities than or comparable to hymexazol, a com. available agricultural fungicide at the concentration of 100 μg/mL. Preliminary structure-activity relationships of antifungal activities were investigated.

Bioorganic & Medicinal Chemistry Letters published new progress about Fungicides. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Product Details of C10H9NO.

Liu, Yuanyuan’s team published research in Chemical Research in Chinese Universities in 2020-10-31 | 950846-89-6

Chemical Research in Chinese Universities published new progress about Fluorescence. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, COA of Formula: C30H36N4O2.

Liu, Yuanyuan; Li, Yi; Zong, Linghui; Zhang, Jingyi published the artcile< Comparison of Two Rhodamine-polyamine Polystyrene Solid-phase Fluorescence Sensors for Hg(II) Detection Based on Theoretical Calculation>, COA of Formula: C30H36N4O2, the main research area is rhodamine polyamine polystyrene fluorescence sensor mercury detection.

Two novel rhodamine-based polystyrene solid-phase fluorescence sensors PS-PA-I and PS-PA-II with different lengths of polyamines were synthesized for Hg(II) determination The detection mechanism involving the Hg(II) chelation-induced spirocycle open of rhodamine was proposed with the aid of theor. calculation The stronger N-Hg bond and the longer polyamine chain in PS-PA-II led to a better selectivity, much higher and more quickly fluorescence response to Hg(II).

Wang, Qinghui’s team published research in Journal of Medicinal Chemistry in 2018-09-13 | 4771-48-6

Journal of Medicinal Chemistry published new progress about Antitumor agents. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Electric Literature of 4771-48-6.

Wang, Qinghui; Arnst, Kinsie E.; Wang, Yuxi; Kumar, Gyanendra; Ma, Dejian; Chen, Hao; Wu, Zhongzhi; Yang, Jinliang; White, Stephen W.; Miller, Duane D.; Li, Wei published the artcile< Structural Modification of the 3,4,5-Trimethoxyphenyl Moiety in the Tubulin Inhibitor VERU-111 Leads to Improved Antiproliferative Activities>, Electric Literature of 4771-48-6, the main research area is trimethoxyphenyl VERU111 synthesis tubulin antitumor.

Colchicine binding site inhibitors (CBSIs) hold great potential in developing new generations of antimitotic drugs. Unlike existing tubulin inhibitors such as paclitaxel, they are generally much less susceptible to resistance caused by the overexpression of drug efflux pumps. The 3,4,5-trimethoxyphenyl (TMP) moiety is a critical component present in many CBSIs, playing an important role in maintaining suitable mol. conformations of CBSIs and contributing to their high binding affinities to tubulin. Previously reported modifications to the TMP moiety in a variety of scaffolds of CBSIs have usually resulted in reduced antiproliferative potency. We previously reported a potent CBSI, VERU-111, that also contains the TMP moiety. Herein, we report the discovery of a VERU-111 analog I that is significantly more potent than VERU-111. The X-ray crystal structure of I in complex with tubulin confirms its direct binding to the colchicine site. In addition, I exhibited a strong inhibitory effect on tumor growth in vivo.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Electric Literature of 4771-48-6.

Huang, Lu-Shan’s team published research in Advanced Synthesis & Catalysis in 2019 | 20870-77-3

Advanced Synthesis & Catalysis published new progress about Bond formation (C-Se). 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, Product Details of C8H6ClNO.

Huang, Lu-Shan; Han, Dong-Yang; Xu, Da-Zhen published the artcile< Iron-Catalyzed Cross-Dehydrogenative Coupling of Oxindoles with Thiols/Selenols for Direct C(sp3)-S/Se Bond Formation>, Product Details of C8H6ClNO, the main research area is oxindole thiol selenol iron catalyst cross dehydrogenative coupling green.

The C-X (S/Se) bonds are common and ubiquitous in natural products and pharmaceuticals. Here, we report an iron-catalyzed cross-dehydrogenative coupling (CDC) reaction for the direct synthesis of C(sp3)-X (S/Se) bonds from oxindoles, phenylacetamides, pyrazolones, phenylacetonitriles and Et cyanoacetate with thiols and selenols. All the reactions were performed under simple and mild conditions, and air (mol. oxygen) was employed as an ideal green oxidant, thus promising broad application in chem. industry and modification of bioactive mols.

Liu, Y’s team published research in Russian Journal of Organic Chemistry in 2021-05-31 | 93247-78-0

Russian Journal of Organic Chemistry published new progress about Aromatic compounds, sulfoxides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Computed Properties of 93247-78-0.

Liu, Y.; Zhang, Z. Y.; Ji, Y. Z.; Li, H. J.; Wu, Y. C. published the artcile< Efficient Synthesis of 3-(Arenesulfinyl)indoles in Water>, Computed Properties of 93247-78-0, the main research area is arenesulfinylindole preparation green chem; indole arylsulfinamide sulfinylation water.

The first example of the sulfinylation of indoles with arylsulfinamides in water in the presence of trifluoroacetic acid as a promoter is described. The reaction occurs smoothly at room temperature under environmentally benign conditions without any catalyst, additive, ligand, or organic solvent. The developed sulfoxide synthetic protocol is attractive due to the use of water as the solvent and provides a novel and efficient route to a wide range of functionalized diaryl sulfoxides.