Indole Building Blocks

Swain, C. J.; Baker, R.; Kneen, C.; Moseley, J.; Saunders, J.; Seward, E. M.; Stevenson, G.; Beer, M.; Stanton, J.; Watling, K. published the artcile< Novel 5-HT3 antagonists. Indole oxadiazoles>, Computed Properties of 23077-43-2, the main research area is hydroxytryptaminergic structure activity indolyloxadiazole oxadiazole; receptor model 5HT3 hydroxytryptamine; antagonist hydroxytryptamine receptor indolyloxadiazole preparation; receptor antagonist hydroxytryptamine oxadiazole preparation.

The synthesis and biochem. evaluation of a series of oxadiazole and indolyloxadiazole 5-HT3 (hydroxytryptamine) antagonists are described. The key pharmacophoric elements have been defined as a basic nitrogen, a linking group capable of H-bonding interactions, and an aromatic moiety. The steric limitations of the aromatic binding site have been determined by substitution about the indole ring. Variation of the heterocyclic linking group has shown that while 2 H-bonding interactions are possible, only 1 is essential for high affinity. The environment of the basic nitrogen has been investigated and shown to be optimal when constrained within an azabicyclic system. These results have been incorporated into a proposed binding model for the 5-HT3 antagonist binding site, in which the optimum distance between the aromatic binding site and the basic amine is 8.4-8.9 Å and the steric limitations are defined by van der Waals difference mapping.

Journal of Medicinal Chemistry published new progress about 5-HT receptors Role: RCT (Reactant), RACT (Reactant or Reagent). 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Computed Properties of 23077-43-2.

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

Wang, Youde; Yan, Zhiwei; Guo, Yachun; Zhang, Liying published the artcile< Discovery and evaluation of novel benzazepinone derivatives as glycogen phosphorylase inhibitors with potent activity>, Recommanded Product: 5-Fluoroindole-2-carboxylic acid, the main research area is benzazepinone derivative glycogen phosphorylase inhibitor hyperglycemia; benzazepinone derivatives; biological activity; glycogen phosphorylase inhibitors; molecular docking; type 2 diabetes.

Glycogen phosphorylase (GP) is a key enzyme of glycogen catabolism, so it is significant to discover a new GP inhibitor. A series of benzazepinone derivatives were discovered as GP inhibitors with potent activity. Among these derivatives, compound 5d showed significant potential against rabbit muscle GPa (IC50 = 0.25 ± 0.05 μM) and cellular efficacy. The in vivo study revealed that 5d significantly inhibited increases in fasting blood glucose level in two kinds of hyperglycemic mice models. The possible binding mode of compound 5d was explored based on mol. docking simulations. These results indicated that derivatives with benzazepinone were potential chem. entities against hyperglycemia.

Future Medicinal Chemistry published new progress about Absorption. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Recommanded Product: 5-Fluoroindole-2-carboxylic acid.

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

Nerella, Ashok; Jeripothula, Madhukar published the artcile< Design, synthesis and biological evaluation of novel deoxyvasicinone-indole as multi-target agents for Alzheimer's disease>, Synthetic Route of 399-76-8, the main research area is oxo tetrahydropyrroloquinazolinyl heteroaryl carboxamide preparation cholinesterase inhibitor mol docking; Acetylcholinesterase inhibitors; Alzheimer’s disease; Deoxyvasicinone; Indole; Multi target agents.

A series of multifunctional hybrids I [R = 1H-indol-2-yl, 1-benzofuran-2-yl, 1-benzothiophen-2-yl, etc.; R1 = H, Me] against Alzheimer’s disease were designed and obtained by conjugating the pharmacophores of deoxyvasicinone and indole. These analogs of deoxyvasicinone-indole were evaluated as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), and as inhibitors of amyloid aggregation (Aβ1-42) for treatment of Alzheimer’s disease (AD). Subsequently, AChE induced Aβ aggregation inhibition test was also performed for selected compounds Biol. activity results demonstrated that compound I [R = 5-methoxy-1H-indol-2-yl, R1 = H] was the most potent and balanced dual ChEs inhibitor with IC50 values 0.12μM and 0.15μM for eeAChE and eqBuChE, resp. Kinetic anal. and docking study indicated that compound I [R = 5-methoxy-1H-indol-2-yl, R1 = H] was a mixed-type inhibitor for both AChE and BuChE. Compound I [R = 5-methoxy-1H-indol-2-yl, R1 = H] also found to be the best inhibitors of self-induced Aβ1-42 aggregation with IC50 values of 1.21μM. Compound I [R = 5-methoxy-1H-indol-2-yl, R1 = H] also afforded excellent inhibition of AChE-induced Aβ1-42 aggregation by 81.1%. Overall, these results indicate that I [R = 5-methoxy-1H-indol-2-yl, R1 = H] may be considered as lead compound for the development of highly effective anti-AD drugs.

Bioorganic & Medicinal Chemistry Letters published new progress about Alzheimer disease. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Synthetic Route of 399-76-8.

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

Sreenivasa Rao, Ramana; Shajan, Femil Joseph; Reddy, D. Srinivasa published the artcile< A route to access imidazol[1,5-a]indole-1,3-diones and pyrrolo[1,2-c]imidazole-1,3-diones>, Electric Literature of 399-76-8, the main research area is imidazolindoledione pyrroloimidazoledione preparation; indole pyrrole carboxylic acid aniline carbonyldiimidazole microwave irradiation.

A novel and practical route to synthesize imidazol[1,5-a]indoles I (R = 3,5-Cl, 4-OCF3, 4-iPr, etc.) and pyrrolo[1,2-c]imidazoles via N-H functionalization has been developed. Indole-2-carboxylic acid or pyrrole-2-carboxylic acid with diverse aniline groups and carbonyldiimidazole (CDI), in the presence of a base under microwave conditions, resulted in imidazol[1,5-a]indoles and pyrrolo[1,2-c]imidazoles, resp. The present method is free of work-up and no need for column chromatog. Both title scaffolds can serve as useful heterocyclic scaffolds in medicinal chem. as such, or they can be used as building blocks to construct different classes of useful compounds

Organic & Biomolecular Chemistry published new progress about Anilines Role: RCT (Reactant), RACT (Reactant or Reagent). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Electric Literature of 399-76-8.

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

Oderinde, Martins S.; Ramirez, Antonio; Dhar, T. G. Murali; Cornelius, Lyndon A. M.; Jorge, Christine; Aulakh, Darpandeep; Sandhu, Bhupinder; Pawluczyk, Joseph; Sarjeant, Amy A.; Meanwell, Nicholas A.; Mathur, Arvind; Kempson, James published the artcile< Photocatalytic Dearomative Intermolecular [2 + 2] Cycloaddition of Heterocycles for Building Molecular Complexity>, HPLC of Formula: 399-76-8, the main research area is regioselective diastereoselective photocatalytic dearomative intermol cycloaddition indole alkene.

Indole and indoline rings are important pharmacophoric scaffolds found in marketed drugs, agrochems., and biol. active mols. The [2 + 2] cycloaddition reaction is a versatile strategy for constructing architecturally interesting, sp3-rich cyclobutane-fused scaffolds with potential applications in drug discovery programs. A general platform for visible-light mediated intermol. [2 + 2] cycloaddition of indoles with alkenes has been realized. A substrate-based screening approach led to the discovery of tert-butyloxycarbonyl (Boc)-protected indole-2-carboxyesters as suitable motifs for the intermol. [2 + 2] cycloaddition reaction. Significantly, the reaction proceeds in good yield with a wide variety of both activated and unactivated alkenes, including those containing free amines and alcs., and the transformation exhibits excellent regio- and diastereoselectivity. Moreover, the scope of the indole substrate is very broad, extending to previously unexplored azaindole heterocycles that collectively afford fused cyclobutane containing scaffolds that offer unique properties with functional handles and vectors suitable for further derivatization. DFT computational studies provide insights into the mechanism of this [2 + 2] cycloaddition, which is initiated by a triplet-triplet energy transfer process. The photocatalytic reaction was successfully performed on a 100 g scale to provide the dihydroindole analog.

Journal of Organic Chemistry published new progress about [2+2] Photocycloaddition reaction (diastereo/regioselective). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, HPLC of Formula: 399-76-8.

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

Li, Man; Yuan, Lan; Chen, Yingying; Ma, Wenxiao; Ran, Fuxiang; Zhang, Lihe; Zhou, Demin; Xiao, Sulong published the artcile< Rhodamine B-based fluorescent probes for molecular mechanism study of the anti-influenza activity of pentacyclic triterpenes>, Application In Synthesis of 950846-89-6, the main research area is rhodamine fluorescent probe preparation pentacyclic triterpene antiviral influenza; Fluorescent probe; Influenza virus; Pentacyclic triterpene; Rhodamine B; Subcellular localization.

The antiviral activity of pentacyclic triterpenes has attracted increasing attention. However, the detailed antiviral mechanism remains fully unclear. In the present study, four C28 or C30 modified pentacyclic triterpene probes via conjugating with rhodamine B were designed and synthesized, and their anti-influenza virus activity was evaluated. The results indicated that two compounds 14 and 23 showed significant antiviral activity to influenza A/WSN/33 (H1N1) virus in Madin-Darby canine kidney (MDCK) cells with IC50 values of 8.36 and 8.24 μM, resp. The mechanism of action studies of representative probe 23 indicated that it could inhibit the membrane fusion by binding with influenza virus hemagglutinin (HA), and the apparent dissociation constant (KD) value for probe 23-HA interaction was successfully evaluated (1.78 x 10-5 M) using surface plasmon resonance spectroscopy. In addition, the subcellular localization of probe 23 in MDCK cells was determined by confocal microscopy and flow cytometry, and the results suggested that fluorescent probe 23 was rapidly taken up in MDCK cells and accumulated in cytoplasm, but no antiviral activity was observed after its entry into cells. The present study further confirmed our previous finding that pentacyclic triterpenes could tightly bind to the viral envelope HA protein, thus blocking the virus entry into host cells.

European Journal of Medicinal Chemistry published new progress about Antiviral agents. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Application In Synthesis of 950846-89-6.

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

Yuan, Wei-Cheng; Zuo, Jian; Yuan, Shu-Pei; Zhao, Jian-Qiang; Wang, Zhen-Hua; You, Yong published the artcile< Ring expansion and ring opening of 3-halooxindoles with N-alkoxycarbonyl-O-tosylhydroxylamines for divergent access to 4-aminoquinolin-2-ones and N-Cbz-N'-arylureas>, SDS of cas: 20870-77-3, the main research area is benzyl oxo aryl dihydroquinolinyl carbamate preparation green chem; benzylidene oxo dihydroquinazoline carboxylate benzyl preparation green chem; benzyloxycarbonyl aryl acetyl phenyl urea preparation green chem; halooxindole alkoxycarbonyl tosylhydroxylamine ring expansion opening.

A divergent method for ring expansion and ring opening of 3-halooxindoles I (X = Cl, Br; R = H, 5-Me, 4-Cl, 5-Br; R1 = H, 3-methylphenyl, ethoxycarbonyl, naphthalen-1-yl, furan-2-yl, etc.) has been developed. Under mild base-mediated conditions, 3-halooxindoles I generate indolones II in situ, which then react smoothly with N-alkoxycarbonyl-O-tosylhydroxylamines R2NH-OTs (R2 = Cbz, Boc) to give 4-aminoquinolin-2-ones III (R3 = H, 6-Me, 5-Cl, 6-Br) and N-Cbz-N’-arylureas IV and V (R4 = H, 4-Me, 4-Br) in good to excellent yields via ring expansion and opening pathways, resp. This protocol is characterized by easy availability of substrates, user-friendly reaction conditions, broad functional group tolerance, and a simple operation procedure.

Organic Chemistry Frontiers published new progress about Benzylidene compounds Role: SPN (Synthetic Preparation), PREP (Preparation). 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, SDS of cas: 20870-77-3.

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

Becker, Daniel P.; Flynn, Daniel L.; Moormann, Alan E.; Nosal, Roger; Villamil, Clara I.; Loeffler, Richard; Gullikson, Gary W.; Moummi, Chafiq; Yang, Dai-C. published the artcile< Pyrrolizidine esters and amides as 5-HT4 receptor agonists and antagonists>, Name: 5-Fluoro-1H-indole-3-carboxylic acid, the main research area is pyrrolizidine arylamide preparation 5HT4 antagonist; arylester pyrrolizidine preparation 5HT4 agonist.

A series of pyrrolizidine esters, amides, and ureas was prepared and tested for 5-HT4 and 5-HT3 receptor binding, 5-HT4 receptor agonism in the rat tunica muscularis mucosae assay (TMM), and for 5-HT3 receptor-mediated functional antagonism in the Bezold-Jarisch reflex assay. Several pyrrolizidine derivatives were identified with high affinity for the 5-HT4 receptor, including benzamide I (SC-53116), a potent and selective 5-HT4 partial agonist that exhibits efficacy in promoting antral contractions and activity in promoting gastric emptying in canine models. Also discovered were 5-HT4 receptor antagonists, including imidazopyridine amide II (SC-53606), which was a potent and selective 5-HT4 receptor antagonist with a pA2 value of 8.13 in the rat TMM assay. N-Me indole ester III was identified as a potent 5-HT4 antagonist with a pA2 value of 8.93. High selectivity was observed for these pyrrolizidine derivatives vs. other monoamine receptors, including 5-HT1, 5-HT2, D1, D2, α1, α2, and β receptors.

Journal of Medicinal Chemistry published new progress about 5-HT receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Name: 5-Fluoro-1H-indole-3-carboxylic acid.

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

Shellaiah, Muthaiah; Thirumalaivasan, Natesan; Aazaad, Basheer; Awasthi, Kamlesh; Sun, Kien Wen; Wu, Shu-Pao; Lin, Ming-Chang; Ohta, Nobuhiro published the artcile< Novel rhodamine probe for colorimetric and fluorescent detection of Fe3+ ions in aqueous media with cellular imaging>, Related Products of 950846-89-6, the main research area is rhodamine probe colorimetry fluorescent iron cell imaging; Colorimetric recognition; Fluorescent “turn-on”; Nanomolar detection; Photoinduced energy transfer; Reversible Fe(3+) sensor; Rhodamine-pyridine conjugate.

A novel rhodamine-pyridine conjugated spectroscopic probe RhP (I) was synthesized and its x-ray single crystalline properties were revealed with tabulation. The RhP displayed a distinct pale-pink colorimetric and “”turn-on”” fluorescent response to Fe3+ in aqueous media [H2O:DMSO (95:5, volume/volume)] than that of other interfering ions. During the Fe3+ recognition, the absorption (UV-visible) and photoluminescence (PL) spectral studies revealed new peaks at 561 and 592 nm, resp. The 1:1 stoichiometry and binding sites were verified by Job′s plot, ESI-mass, and 1H NMR titrations Subsequently, LOD and binding constant for RhP + Fe3+ complex were estimated as 102.3 nM and 6.265 × 104 M-1 from linear fitting and Benesi-Hildebrand plots, correspondingly. Sensor reversibility of RhP + Fe3+ by EDTA was demonstrated by UV/PL and TRPL studies. Moreover, the photoinduced energy transfer mechanism and band gap changes were established from the DFT interrogations. Lastly, cellular imaging studies were carried out to authenticate the real applicability of RhP in Fe3+ detection.

Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy published new progress about Colorimetry. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Related Products of 950846-89-6.

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

Luo, Yang-Hui; Sun, Bai-Wang published the artcile< An investigation into the substituent effect of halogen atoms on the crystal structures of indole-3-carboxylic acid (ICA)>, Application of C9H6FNO2, the main research area is halogen atom crystal structure indolecarboxylic acid ICA.

A study into the substituent effect of halogen atoms (F, Cl, Br) on the crystal structure of indole-3-carboxylic acid (ICA) was prepared The study was done through the aspect of crystal structure, intermol. interactions and π···π stacking motifs with the assistance of IR spectra, elemental analyses, NMR spectra, DSC, thermogravimetric analyses (TGA) and hot stage microscopy (HSM) measurements. The different kinds of halogen atoms and the different substituted positions have a significant effect on the crystal structures, mol. π···π stacking motifs and the kinds of intermol. interactions. The authors further correlated the m.ps. of the ICAs with the H-H, O-H and X-H (X = F, Cl, Br) interactions, and found a pos. correlation between them.

CrystEngComm published new progress about Correlation analysis. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Application of C9H6FNO2.

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