Indole Building Blocks

Liu, Boya’s team published research in ACS Applied Polymer Materials in 2022-09-09 | 399-76-8

ACS Applied Polymer Materials published new progress about Crosslinking. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Safety of 5-Fluoroindole-2-carboxylic acid.

Liu, Boya; Liu, Yang; Liu, Xiangyang published the artcile< Enhanced Thermal Conductivity of All-Organic Aramid Nanofiber Films via Interfacial Coupling Reaction>, Safety of 5-Fluoroindole-2-carboxylic acid, the main research area is thermal conductivity organic aramid nanofiber film interfacial coupling.

It is still a great challenge to prepare intrinsically all-organic thermal conductive membrane with high in-plane and through-plane thermal conductivity Herein, we designed an all-organic aramid nanofiber thin film with in-plane and through-plane thermal conductivity as high as 15.7 and 0.26 W/mK, resp., through one step fluorination utilizing F2/N2. We proved that direct fluorination could induce the coupling reaction of benzene rings in neighboring aramid macromols. to form numerous covalent crosslinking bonds among aramid nanofibers. Benefiting from the crosslinking behavior, interfacial thermal resistance between the nanofibers was suppressed to some extent, thereby leading to enhancement of in-plane and through-plane thermal conductivity by 78.8% and 271.7%, resp., compared with the unmodified membranes. In addition, the thin films also possess high mech. strength and elec. insulation, which promote its application potential in flexible electronic fields.

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

Zi, Weiwei’s team published research in Journal of the American Chemical Society in 2015-03-11 | 4771-48-6

Journal of the American Chemical Society published new progress about Acetals Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (indolyl, propargyl). 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Category: indole-building-block.

Zi, Weiwei; Wu, Hongmiao; Toste, F. Dean published the artcile< Gold(I)-Catalyzed Dearomative Rautenstrauch Rearrangement: Enantioselective Access to Cyclopenta[b]indoles>, Category: indole-building-block, the main research area is cyclopentaindole cyclopentapyrrole enantioselective diastereoselective preparation; stereoselective Rautenstrauch rearrangement indolylpropynyl pyrrolylpropynyl acetal Segphos digold complex; dearom diastereoselective enantioselective Rautenstrauch rearrangement indolylpropynyl pyrrolylpropynyl acetal; methylcyclopentaindolecarboxylate mol crystal structure.

In the presence of a DTBM-Segphos digold complex and AgSbF6, indolylpropynyl acetals I (R = H, 5-F, 5-Br, 5-Me, 5-MeO, 4-Me, 6-MeO, 6-Cl, 7-Me; R1 = Me, Et, Bu; R3 = MeO2C, EtO2C, H2C:CHCH2O2C, EtCO, PhCO; Ts = 4-MeC6H4SO2) and a pyrrolylpropynyl acetal underwent enantioselective dearomative Rautenstrauch rearrangements to yield (after hydrolysis) nonracemic cyclopenta[b]indoles II (R = H, 5-F, 5-Br, 5-Me, 5-MeO, 4-Me, 6-MeO, 6-Cl, 7-Me; R1 = Me, Et, Bu; R3 = MeO2C, EtO2C, H2C:CHCH2O2C, EtCO, PhCO) and a cyclopentapyrrolecarboxylate in 46-91% yields and in 71-98% ee. The structures of II (R = 4-Me; R1 = Me; R2 = MeO2C) and of a reduction product derived from II (R = H; R1 = Me; R2 = MeO2C) were determined by X-ray crystallog.

Henderson, Scott H’s team published research in Royal Society Open Science in 2018 | 23077-43-2

Royal Society Open Science published new progress about Decarboxylation (halo). 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Application In Synthesis of 23077-43-2.

Henderson, Scott H.; West, Ryan A.; Ward, Simon E.; Honey, Mark A. published the artcile< Metal-free selective mono-halodecarboxylation of heteroarenes under mild conditions>, Application In Synthesis of 23077-43-2, the main research area is haloheteroarene preparation; heteroarene carboxylic acid mono halodecarboxylation; halodecarboxylation; mild conditions; selective halogenation.

A mild and efficient protocol was developed for the synthesis of haloheteroarenes such as I [R = H, 5-F, 5-NO2, etc.; R1 = Cl, Br; X = C, N] via mono-halodecarboxylation of heteroarene carboxylic acids by treatment with N-bromosuccinimide or N-chlorosuccinimide. This method was metal-free and displayed significant advantages over traditional halodecarboxylation procedures that require expensive and toxic metal catalysts, basic conditions, time-consuming intermediate isolation and elevated reaction temperatures

Palani, Vignesh’s team published research in Chemical Science in 2021 | 93247-78-0

Chemical Science published new progress about Fused heterocyclic compounds Role: PRP (Properties), 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, Safety of Methyl 1H-indole-7-carboxylate.

Palani, Vignesh; Perea, Melecio A.; Gardner, Kristen E.; Sarpong, Richmond published the artcile< A pyrone remodeling strategy to access diverse heterocycles: application to the synthesis of fascaplysin natural products>, Safety of Methyl 1H-indole-7-carboxylate, the main research area is fascaplysin preparation; pyridoindole preparation.

The synthesis of diverse N-fused heterocycles, including the pyrido[1,2-a]indole scaffold, e.g., I, using an efficient pyrone remodeling strategy was described. The pyrido[1,2-a]indole core was demonstrated to be a versatile scaffold that could be site-selectively functionalized. The utility of this novel annulation strategy was showcased in a concise formal synthesis of three fascaplysin congeners.

Iioka, Ryoya’s team published research in European Journal of Organic Chemistry in 2021-03-08 | 399-76-8

European Journal of Organic Chemistry published new progress about Antitumor agents. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Category: indole-building-block.

Iioka, Ryoya; Yorozu, Kohei; Sakai, Yoko; Kawai, Rika; Hatae, Noriyuki; Takashima, Katsuki; Tanabe, Genzoh; Wasada, Hiroaki; Yoshimatsu, Mitsuhiro published the artcile< Synthesis of azepino[1,2-a]indole-10-amines via [6+1] annulation of ynenitriles with Reformatsky reagent>, Category: indole-building-block, the main research area is azepinoindoleamine preparation annulation Lewis acid catalysis.

Lewis acid-catalyzed [6+1] annulation reactions of 2-cyano-1-propargyl- and 2-alkynyl-1-cyanomethyl-indoles with Reformatsky reagent are described. 8-Aryl, 8-alkyl-, 8-hetaryl-, 9-aryl, and 9-alkyl-azepino[1,2-a]indole amines were obtained through a 7-endo-mode cyclization of the β-aminoacrylate intermediates. The antiproliferative activity of the azepino[1,2-a]indoles analogs against the HCT-116 cells were also examined

Tran, Quy Thi Ngoc’s team published research in European Journal of Medicinal Chemistry in 2022-02-15 | 20870-77-3

European Journal of Medicinal Chemistry published new progress about Antiviral agents. 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, COA of Formula: C8H6ClNO.

Tran, Quy Thi Ngoc; Lee, Regina Ching Hua; Liu, Hon Jin; Ran, Danli; Low, Vincent Zhan Lin; To, Dong Quang; Chu, Justin Jang Hann; Chai, Christina Li Lin published the artcile< Discovery and development of labdane-oxindole hybrids as small-molecule inhibitors against chikungunya virus infection>, COA of Formula: C8H6ClNO, the main research area is chikungunya virus infection labdane oxindole hybrid; Antiviral; Arbovirus; Chikungunya; Labdane diterpenoid; Oxindole.

Chikungunya virus (CHIKV) infection, a febrile illness caused by a mosquito-transmitted alphavirus, has afflicted millions of people worldwide. There is currently no approved effective antiviral treatment for CHIKV infection. In this study, we report a new class of small-mol. CHIKV inhibitors, the oxindole-labdanes, that potently block the replication of CHIKV with good selectivity. Andrographolide, a previously reported inhibitor of CHIKV infection, was used as the lead compound for our initial structure-activity relationship (SAR) study. From a focused library of 72 andrographolide analogs, we identified the lead compound (E)-2 with improved antiviral activities. Further optimization of (E)-2 led to the discovery of the normal-labdane 7-chloro-oxindole (E)-42 as potent inhibitor against two low-passage CHIKV isolates from human patients with an EC50 of 1.55 μM against CHIKV-122508 and 0.14 μM against CHIKV-6708. Compound (E)-42 displayed minimal cytotoxic liability (CC50 > 100 μM), thus furnishing good selectivity relative to the host cells. Mechanistically, (E)-42 does not inactivate the viral particles but rather acts on the host cells to interfere with the viral replication, demonstrating both prophylactic and therapeutic effects. Our findings open a new avenue for the development of oxindole-labdane compounds as promising antiviral drugs against CHIKV infection.

Yoo, Woo-Jin’s team published research in Organic Letters in 2012-10-19 | 23077-43-2

Organic Letters published new progress about Carboxylation. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Computed Properties of 23077-43-2.

Yoo, Woo-Jin; Capdevila, Montse Guiteras; Du, Xiangwei; Kobayashi, Shu published the artcile< Base-Mediated Carboxylation of Unprotected Indole Derivatives with Carbon Dioxide>, Computed Properties of 23077-43-2, the main research area is indole carboxylic acid preparation; base carboxylation unprotected indole carbon dioxide.

A simple and straightforward method for the preparation of indole-3-carboxylic acids was discovered through the direct carboxylation of indoles with atm. pressure of carbon dioxide (CO2) under basic conditions. The key for the reaction was found to be the use of a large excess of LiOtBu as a base to suppress the undesired decarboxylation side reaction.

Organic Letters published new progress about Carboxylation. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Computed Properties of 23077-43-2.

Hrizi, Asma’s team published research in Molecules in 2021 | 399-76-8

Molecules published new progress about Alkenes 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, Reference of 399-76-8.

Hrizi, Asma; Cailler, Manon; Romdhani-Younes, Moufida; Carcenac, Yvan; Thibonnet, Jerome published the artcile< Synthesis of New Highly Functionalized 1H-Indole-2-carbonitriles via Cross-Coupling Reactions>, Reference of 399-76-8, the main research area is alkenyl indole carbonitrile preparation; aryl indole carbonirile preparation; 1H-indole-2-carbonitriles; Heck; Sonogashira; Stille; Suzuki–Miyaura.

An approach for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction of compounds 1-(but-2-ynyl)-1H-indole-2-carbonitriles and 1-benzyl-3-iodo-1H-indole-2-carbonitriles was described. The reactivity of indole derivatives with iodine at position 3 was studied using cross-coupling reactions. The Sonogashira, Suzuki-Miyaura, Stille and Heck cross-couplings afforded a variety of di-, tri- and tetra-substituted indole-2-carbonitriles.

Wu, Ke-Xin’s team published research in Green Chemistry in 2021 | 20870-77-3

Green Chemistry published new progress about Arylation (chemoselective). 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, Computed Properties of 20870-77-3.

Wu, Ke-Xin; Xu, Yi-Ze; Cheng, Liang; Wu, Run-Shi; Liu, Peng-Ze; Xu, Da-Zhen published the artcile< Iron-catalyzed oxidative bis-arylation of indolin-2-ones for direct construction of quaternary carbons>, Computed Properties of 20870-77-3, the main research area is oxindole bis indolyl preparation chemoselective green chem; indolinone indole oxidative bis arylation iron catalyst.

A direct construction of all-carbon quaternary centers from secondary C(sp3)-H substrates through a dehydrogenative cross-coupling reaction was described. Using FeCl2·4H2O as the catalyst and employing air (mol. oxygen) as the terminal oxidant, the cross-coupling of indolin-2-ones I (R1 = H, Me, Ph, Bn; R2 = H, 6-Cl, 5-F, etc.) with indoles such as 5-fluoroindole, N-methylindole, 3-methylindole, etc. proceeded smoothly under mild, ligand-free and base-free conditions, providing 3,3-disubstituted oxindoles bearing all-carbon quaternary centers II (R3 = 5-fluoroindol-3-yl, N-methylindol-3-yl, 3-methylindol-2-yl, etc.) with excellent chemoselectivities.

Green Chemistry published new progress about Arylation (chemoselective). 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, Computed Properties of 20870-77-3.

Ghosh, Ayndrila’s team published research in Tetrahedron Letters in 2020-02-27 | 950846-89-6

Tetrahedron Letters published new progress about Fluorescence imaging. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Product Details of C30H36N4O2.

Ghosh, Ayndrila; Mandal, Saurodeep; Das, Sujoy; Shaw, Pallab; Chattopadhyay, Ansuman; Sahoo, Prithidipa published the artcile< Insights into the phenomenon of acquisition and accumulation of Fe3+ in Hygrophila spinosa through fluorimetry and fluorescence images>, Product Details of C30H36N4O2, the main research area is Hygrophila ferric uptake fluorescent probe imaging.

Rhodamine functionalized fluorescent probe IP has been synthesized to investigate the phenomenon of Fe3+ acquisition and accumulation in Hygrophila spinosa. H. spinosa is a tropical medicinal plant which is iron rich and consumed for the treatment of the patients suffering from anemia. IP is capable of selectively binding Fe3+ by enhancing fluorescent intensity via “”turn on”” mechanism due to complex formation. Spectroscopic studies and microscopic tools helped in better understanding about the acquisition as well as the quant. accumulation of Fe3+ in different parts of the plant.

Tetrahedron Letters published new progress about Fluorescence imaging. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Product Details of C30H36N4O2.