Category: 20870-77-3

Woldegiorgis, Alemayehu Gashaw; Han, Zhao; Lin, Xufeng published the artcile< Asymmetric [3 + 3] Annulation to Construct Trifluoromethylated Pyrazolo[3,4-b]pyridin-6-ones via Chiral Phosphoric Acid and MgSO4 Synergistic Catalysis>, Reference of 20870-77-3, the main research area is trifluoromethyl pyrazolopyridinone preparation enantioselective diastereoselective; aminopyrazole trifluoroethylidene oxindole Friedel Crafts alkylation transamidation phosphoric acid.

A novel asym. Friedel-Crafts alkylation/transamidation tandem reaction for the enantio- and diastereoselective synthesis of pyrazolo[3,4-b]pyridin-6-ones I (R = H, Me, Cl; R1 = H, OMe, Br, Cl, F; R2 = H, Me, Br, F; R3 = H, Br; R4 = Boc, Cbz; R5 = H, Et, i-Pr; R6 = Ph, 3-bromophenyl, 1H-benzo[d]imidazol-2-yl, etc.; R7 = Me, Et, i-Pr, Ph) bearing a -CF3 unit via synergistic chiral phosphoric acid and MgSO4 catalysis was developed. This [3 + 3] annulation protocol allows the formation of trifluoromethylated pyrazolo[3,4-b]pyridin-6-ones I with two adjacent tertiary stereocenters in moderate to high yields (up to 90%), enantioselectivities (up to 97% ee), and diastereoselectivities (up to >20:1 dr).

Organic Letters published new progress about Diastereoselective synthesis. 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, Reference of 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

Qin, Hui; Li, Qi; Xu, Jian; Zhang, Jie; Qu, Wei; Liu, Wenyuan; Feng, Feng; Sun, Haopeng published the artcile< A Mild and Direct C(sp3)-S Cross-Coupling of Oxindoles with Thiols: Synthesis of Unsymmetrical 3-Thiooxindoles>, Application In Synthesis of 20870-77-3, the main research area is thiooxindole preparation coupling oxindole thiol.

Herein, an operationally simple and mild strategy to construct sulfenation of oxindoles with a series of thiols in the absence of transition metals was developed. This methodol. provides an efficient way to directly form a C-S bond at the C-3 position of oxindoles under mild reaction conditions with a cheap and common solvent and base in moderate to good yields.

Journal of Organic Chemistry published new progress about Cross-coupling reaction. 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, Application In Synthesis of 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

Liu, Li; Li, Yue; Wang, Feng; Ning, Rui; Kong, Dulin; Wu, Mingshu published the artcile< A new synthetic approach to oxindoles (1,3-dihydro-2H-indol-2-ones) by reductive dephosphorylation with hydroiodic acid of 3-(diethylphosphoryloxy)-oxindoles, derived from isatins (1H-Indole-2,3-diones)>, Category: indole-building-block, the main research area is diethylphosphoryloxy oxindole preparation reductive dephosphorylation; oxindole preparation.

A novel method for the synthesis of 3-unsubstituted oxindoles by the reductive dephosphorylation of 3-(diethylphosphoryloxy)oxindoles with hydroiodic acid was developed. This synthetic strategy involved a two-step procedure including a phospha-Brook rearrangement of isatins with di-Et phosphite and a reductive dephosphorylation of the phosphorylated oxindoles.

ARKIVOC (Gainesville, FL, United States) published new progress about Dephosphorylation (reductive). 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, Category: indole-building-block.

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

Morigi, Rita; Locatelli, Alessandra; Leoni, Alberto; Rambaldi, Mirella; Bortolozzi, Roberta; Mattiuzzo, Elena; Ronca, Roberto; Maccarinelli, Federica; Hamel, Ernest; Bai, Ruoli; Brancale, Andrea; Viola, Giampietro published the artcile< Synthesis, in-vitro and in-vivo biological evaluation of substituted 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones as new potent anticancer agents>, Related Products of 20870-77-3, the main research area is imidazothiazolylmethylene indolinone preparation antitumor activity SAR cytotoxicity apoptosis; 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones; Antiproliferative; Antitumor; Apoptosis; Synthesis.

A small library of 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones were synthesized and screened according to protocols available at the National Cancer Institute (NCI). Some derivatives were potent antiproliferative agents, showing GI50 values in the nanomolar range. Remarkably, when most active compounds against leukemia cells were tested in human peripheral blood lymphocytes from healthy donors, were 100-200 times less cytotoxic. Some compounds, selected by the Biol. Evaluation Committee of NCI, were examined to determine tubulin assembly inhibition. Furthermore, flow cytometric studies performed on HeLa, HT-29, and A549 cells, showed that compounds and caused a block in the G2/M phase. Interestingly, these derivatives induced apoptosis through the mitochondrial death pathway, causing in parallel significant activation of both caspase-3 and -9, PARP cleavage and down-regulation of the anti-apoptotic proteins Bcl-2 and Mcl-1. Finally, compound was also tested in-vivo in the murine BL6-B16 melanoma and E0771 breast cancer cells, causing in both cases a significant reduction in tumor volume

European Journal of Medicinal Chemistry published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, Related Products of 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

Cockerill, G. Stuart; Angell, Richard M.; Bedernjak, Alexandre; Chuckowree, Irina; Fraser, Ian; Gascon-Simorte, Jose; Gilman, Morgan S. A.; Good, James A. D.; Harland, Rachel; Johnson, Sara M.; Ludes-Meyers, John H.; Littler, Edward; Lumley, James; Lunn, Graham; Mathews, Neil; McLellan, Jason S.; Paradowski, Michael; Peeples, Mark E.; Scott, Claire; Tait, Dereck; Taylor, Geraldine; Thom, Michelle; Thomas, Elaine; Villalonga Barber, Carol; Ward, Simon E.; Watterson, Daniel; Williams, Gareth; Young, Paul; Powell, Kenneth published the artcile< Discovery of Sisunatovir (RV521), an Inhibitor of Respiratory Syncytial Virus Fusion>, Reference of 20870-77-3, the main research area is Sisunatovir analog drug discovery synthesis RSV antiviral.

RV521 is an orally bioavailable inhibitor of respiratory syncytial virus (RSV) fusion that was identified after a lead optimization process based upon hits that originated from a phys. property directed hit profiling exercise at Reviral. This exercise encompassed collaborations with a number of contract organizations with collaborative medicinal chem. and virol. during the optimization phase in addition to those utilized as the compound proceeded through preclin. and clin. evaluation. RV521 exhibited a mean IC50 of 1.2 nM against a panel of RSV A and B laboratory strains and clin. isolates with antiviral efficacy in the Balb/C mouse model of RSV infection. Oral bioavailability in preclin. species ranged from 42 to >100% with evidence of highly efficient penetration into lung tissue. In healthy adult human volunteers exptl. infected with RSV, a potent antiviral effect was observed with a significant reduction in viral load and symptoms compared to placebo.

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, Reference of 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

Treuerne Balazs, Krisztina E.; Molnar, Mark; Madarasz, Zoltan; Nyerges, Miklos published the artcile< A facile synthesis of novel polycyclic spiropyrrolidine oxindoles incorporating the 1,3-dipolar cycloaddition of azomethine ylides>, Product Details of C8H6ClNO, the main research area is polycyclic spiropyrrolidine oxindole preparation regio diastereoselective; azomethine ylide arylmethylene indolinone dipolar cycloaddition.

This study describes the synthesis of novel polycyclic spiropyrrolidine oxindoles through the 1,3-dipolar cycloaddition of azomethine ylides generated in situ with 3-(arylmethylene)-indolin-2-ones. Effect of substituents of azomethine ylides and various dipolarophiles on reactivity, as well as on the products regio- and stereoselectivity was investigated.

Synthetic Communications published new progress about 1,3-Dipolar cycloaddition reaction, regioselective. 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, Product Details of C8H6ClNO.

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

Hu, Ren-Ming; Han, Dong-Yang; Li, Ning; Huang, Jie; Feng, Yu; Xu, Da-Zhen published the artcile< Iron-Catalyzed Direct Oxidative Alkylation and Hydroxylation of Indolin-2-ones with Alkyl-Substituted N-Heteroarenes>, Category: indole-building-block, the main research area is iron catalyzed oxidative oxidative alkylation hydroxylation indolinone alkylheteroarene; N-heteroarenes; cross-coupling; iron; molecular oxygen; oxidation.

Presented herein is the first direct alkylation and hydroxylation reaction between two different C(sp3)-H bonds, indolin-2-ones and alkyl-substituted N-heteroarenes, through an oxidative cross-coupling reaction. The reaction is catalyzed by a simple iron salt under mild ligand-free and base-free conditions. The reaction is environmentally benign, employs air (mol. oxygen) as the terminal oxidant and oxygen source for the synthesis of O-containing compounds, and produces only water as the byproduct. Thus, e.g., indolin-2-one + 2-methylquinoline → I (93%) in presence of Fe(OAc)2.

Angewandte Chemie, International Edition published new progress about Alkylarenes Role: RCT (Reactant), RACT (Reactant or Reagent) (alkyl-substituted N-heteroarenes). 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, Category: indole-building-block.

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

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.

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.

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

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.

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, Ruo-Pu; Wang, Zheng-Lin; Zhang, Yun-Hao; Tan, Zhi-Yu; Xu, Da-Zhen published the artcile< Iodine-Catalyzed Oxidative Coupling of Indolin-2-ones with Indoles: Synthesis of 3,3-Disubstituted Oxindole Compounds>, Application of C8H6ClNO, the main research area is disubstituted oxindole preparation; indolinone indole oxidative coupling iodine catalyst.

Here, an iodine-catalyzed oxidative coupling of indolinones with indoles for the construction of compounds with all-carbon quaternary centers such as 1H,1”H-[3,3′:3′,3”-terindol]-2′(1’H)-ones I [R1 = H, Me, Bn, etc.; R2 = H, 5-Br, 5-F, etc.; R3 = H, Me, R4 = H, 2-Me, 5-OMe, etc.] was described. The method performed under metal-free and peroxide-free conditions, providing 3,3-disubstituted oxindoles via two C-C bond formations from secondary C(sp3)-Hs in a straightforward manner.

ChemistrySelect published new progress about C-C bond formation. 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, Application of C8H6ClNO.

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