116325-12-3

Usage

Derivative of indole

a common component of many natural compounds and pharmaceuticals

Unique structure

presence of a phenylsulfonyl group at the 1-position and a methyl group at the 5-position

Potential pharmaceutical applications

the phenylsulfonyl group can influence chemical reactivity and biological activity

Utilization in medicinal chemistry and drug discovery research

for the development of new pharmaceuticals with potential therapeutic benefits.

Upstream product

• 97188-21-1 3-nitro-1-(phenylsulfonyl)-1H-pyrrole 
• 78-79-5 isoprene 
• 614-96-0 5-methyl-1H-indole 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 83372-78-5 1-Benzenesulfonyl-5-methyl-1,2-dihydro-indol-3-one 
• 1196-79-8 2,5-Dimethyl-1H-indole 
• 700836-86-8 1-benzenesulfonyl-2,5-dimethyl-1H-indole 
• 1184953-71-6 5-(bromomethyl)-1-(phenylsulfonyl)-1H-indole 
• 231297-02-2 2-(4-chlorobenzoyl)-5-methyl-1-(phenylsulfonyl)indole 
• 405917-83-1 (5-methyl-1-phenylsulfonyl-1H-2-indolyl)(1-phenylsulfonyl-1H-2-indolyl)methanone 
• 896138-25-3 (5-benzyloxy-1H-indol-2-yl)-(5-methyl-1H-indol-2-yl)methanone 
• 896137-97-6 (5-benzyloxy-1-phenylsulfonyl-1H-indol-2-yl)-(5-methyl-1-phenylsulfonyl-1H-indol-2-yl)methanone 
• 405917-82-0 (5-methyl-1-phenylsulfonyl-1H-2-indolyl)(1-phenylsulfonyl-1H-2-indolyl)methanol 
• 370580-30-6 2-methoxyphenyl-(5-methyl-1-phenylsulfonyl-1H-2-indolyl)-methanone 

Relevant academic research and scientific papers

[Copper(I)(Pyridine-Containing Ligand)] Catalyzed Regio- and Steroselective Synthesis of 2-Vinylcyclopropa[b]indolines from 2-Vinylindoles

A [copper(I)pyridine-containing ligand]-catalyzed reaction between 2-vinylindoles and diazo esters is described. The reaction allows for the synthesis of a series of 2-vinylcyclopropa[b]indolines with excellent levels of regio- and sterocontrol under mild

Construction of Oxepino[3,2-b]indoles via [4+3] Annulation of 2-Ylideneoxindoles with Crotonate-Derived Sulfur Ylides

A [4+3] annulation of 2-ylideneoxindoles with crotonate-derived sulfur ylides has been developed. A series of oxepino[3,2-b]indoles were prepared in moderate to excellent yields (62-93%) under mild conditions. Moreover, the synthetic oxepino[3,2-b] indoles can be further transformed into more complex cyclopropa[5,6]oxepino[3,2-b]indoles via a [2+1] cyclopropanation. In addition, the synthetic compounds show certain antiproliferative activity against K562 and MCF-7 cells, and its IC50 values for these two kinds of tumor cells up to 5.40±0.88 μM and 18.41±0.50 μM, respectively. (Figure presented.).

Discovery of a First-in-Class, Potent, Selective, and Orally Bioavailable Inhibitor of the p97 AAA ATPase (CB-5083)

The AAA-ATPase p97 plays vital roles in mechanisms of protein homeostasis, including ubiquitin-proteasome system (UPS) mediated protein degradation, endoplasmic reticulum-associated degradation (ERAD), and autophagy. Herein we describe our lead optimization efforts focused on in vitro potency, ADME, and pharmaceutical properties that led to the discovery of a potent, ATP-competitive, D2-selective, and orally bioavailable p97 inhibitor 71, CB-5083. Treatment of tumor cells with 71 leads to significant accumulation of markers associated with inhibition of UPS and ERAD functions, which induces irresolvable proteotoxic stress and cell death. In tumor bearing mice, oral administration of 71 causes rapid accumulation of markers of the unfolded protein response (UPR) and subsequently induces apoptosis leading to sustained antitumor activity in in vivo xenograft models of both solid and hematological tumors. 71 has been taken into phase 1 clinical trials in patients with multiple myeloma and solid tumors.

A Palladium(II)-Catalyzed C-H Activation Cascade Sequence for Polyheterocycle Formation

Polyheterocycles are found in many natural products and are useful moieties in functional materials and drug design. As part of a program towards the synthesis of Stemona alkaloids, a novel palladium(II)-catalyzed C-H activation strategy for the construction of such systems has been developed. Starting from simple 1,3-dienyl-substituted heterocycles, a large range of polycyclic systems containing pyrrole, indole, furan and thiophene moieties can be synthesized in a single step. Don't overdo it: A palladium(II)-catalyzed C-H activation cascade sequence for the synthesis of polyheterocycles is reported. Aromatization of the initially formed dihydro species occurred with a quinone oxidant. In some cases the use of one equivalent of the oxidant enabled isolation of the dihydro species as a single isomer (see scheme; X=NMe, O, S).

Substituted 4-aminocyclohexane derivatives

Substituted 4-aminocyclohexane derivatives having the formula I: [image] wherein R1-R4 are as described herein, methods for their preparation, medicinal products and pharmaceutical compositions containing these compounds and the use of substituted 4-amino

Novel bis(1H-indol-2-yl)methanones as potent inhibitors of FLT3 and platelet-derived growth factor receptor tyrosine kinase

FLT3 receptor tyrosine kinase is aberrantly active in many cases of acute myeloid leukemia (AML). Recently, bis(1H-indol-2-yl)methanones were found to inhibit FLT3 and PDGFR kinases. To optimize FLT3 activity and selectivity, 35 novel derivatives were synthesized and tested for inhibition of FLT3 and PDGFR autophosphorylation. The most potent FLT3 inhibitors 98 and 102 show IC 50 values of 0.06 and 0.04 μM, respectively, and 1 order of magnitude lower PDGFR inhibiting activity. The derivatives 76 and 82 are 20- to 40-fold PDGFR selective. Docking at the recent FLT3 structure suggests a bidentate binding mode with the backbone of Cys-694. Activity and selectivity can be related to interactions of one indole moiety with a Hydrophobic pocket including Phe-691, the only different binding site residue (PDGFR Thr-681). Compound 102 inhibited the proliferation of 32D cells expressing wildtype FLT3 or FLT3-ITD similarly as FLT3 autophosphorylation, and induced apoptosis in primary AML patient blasts.