104291-81-8 | - Indole Building Blocks

Roever, S.’s team published research in Bioorganic & Medicinal Chemistry Letters in 2005-08-01 | CAS: 104291-81-8

Bioorganic & Medicinal Chemistry Letters published new progress about 5-HT2C agonists. 104291-81-8 belongs to class indole-building-block, name is Ethyl 6-cyano-1H-indole-2-carboxylate, and the molecular formula is C12H10N2O2, Recommanded Product: Ethyl 6-cyano-1H-indole-2-carboxylate.

Roever, S. published the artcileIdentification of 4-methyl-1,2,3,4,10,10a-hexahydropyrazino[1,2-a]indoles as 5-HT2C receptor agonists, Recommanded Product: Ethyl 6-cyano-1H-indole-2-carboxylate, the main research area is pyrazinoindole hexahydro preparation 5HT2C receptor agonist.

Synthesis and evaluation of the activity of new 4-methyl-1,2,3,4,10,10a-hexahydropyrazino[1,2-a]indoles as 5-HT2C receptor agonists are described. Appropriately substituted, several analogs, e.g. I, displayed selectivity against the other 5-HT2 receptor subtypes of 1 order of magnitude or more. Selectivity was improved for several compounds vs. the lead II, increasing the therapeutic interest in this series of 5-HT2C receptor agonists.

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

Huang, Wenrong’s team published research in Bioorganic & Medicinal Chemistry Letters in 2003-02-10 | CAS: 104291-81-8

Bioorganic & Medicinal Chemistry Letters published new progress about Anticoagulants. 104291-81-8 belongs to class indole-building-block, name is Ethyl 6-cyano-1H-indole-2-carboxylate, and the molecular formula is C12H10N2O2, Related Products of indole-building-block.

Huang, Wenrong published the artcileDesign, synthesis and structure-activity relationships of benzoxazinone-based factor Xa inhibitors, Related Products of indole-building-block, the main research area is benzoxazinone derivative preparation structure Activity relationship factor Xa inhibitor.

A series of benzoxazinone derivatives was designed and synthesized as factor Xa inhibitors. We demonstrated that the naphthyl moiety in two aniline-based compounds can be replaced with benzene-fused heterobicycles and biaryls to give factor Xa inhibitors with improved trypsin selectivity. The P4 modifications lead to monoamidines which are moderately active. The prepared benzoxazinones are potent against factor Xa, retain the improved trypsin selectivity of the corresponding aniline-based compounds, and show strong antithrombotic effect dose responsively.

Ono, Shin’ichiro’s team published research in Chemical & Pharmaceutical Bulletin in 1999-12-31 | CAS: 104291-81-8

Chemical & Pharmaceutical Bulletin published new progress about Anticoagulants. 104291-81-8 belongs to class indole-building-block, name is Ethyl 6-cyano-1H-indole-2-carboxylate, and the molecular formula is C12H10N2O2, Application of Ethyl 6-cyano-1H-indole-2-carboxylate.

Ono, Shin’ichiro published the artcilePreparation and pharmacological evaluation of novel glycoprotein (Gp) IIb/IIIa antagonists. 2. Condensed heterocyclic derivatives, Application of Ethyl 6-cyano-1H-indole-2-carboxylate, the main research area is benzofuran preparation structure integrin antagonist antithrombotic; platelet aggregation inhibitor integrin receptor antagonist; prodrug amidinobenzofuran integrin antagonist antithrombotic.

A novel series of platelet receptor glycoprotein (Gp) IIb/IIIa antagonists with condensed heterocycles as their basic core was synthesized. In an in vitro assay, trans-4-(5-amidinobenzofuran-2-carboxamido)cyclohexyloxyacetic acid (I) and trans-3-[4-(5-amidinobenzofuran-2-carboxamido)cyclohexyl]propionic acid (II) produced marked inhibitions with IC50 values of 0.018 and 0.006 μM, resp., in a human platelet adenosine-5′-diphospate (ADP)-induced aggregation assay; they also exhibited a wide spectrum of inhibition toward major aggregation agonists (ADP, collagen, thrombin, PMA (tumor promoter) and arachidonic acid). These compounds were >2-3 orders of magnitude more effective in inhibiting platelet aggregation than human umbilical vein endothelial cell (HUVEC) binding. The oral administration of 10 mg/kg of either I and II to guinea pig, resulted in a 60% inhibition of ex vivo platelet aggregation after 5 h. Oral administration of Et trans-4-(5-amidinobenzofuran-2-carboxamido)cyclohexyloxyacetate (III) (10 mg/kg) resulted in 80% inhibition of platelet aggregation in dogs for 6 h after oral administration with a return to baseline by 24 h. Et trans-3-[4-(5-amidinobenzofuran-2-carboxamido)cyclohexyl]propionate (AR0598) produced 80% inhibition for 5 h after oral administration. Prodrug III showed a good profile in dogs with a long duration of action. III (AR0510) was selected as suitable clin. candidate for development as an orally active antithrombotic agent.

Sall, Daniel J.’s team published research in Journal of Medicinal Chemistry in 1997-08-29 | CAS: 104291-81-8

Journal of Medicinal Chemistry published new progress about Blood platelet. 104291-81-8 belongs to class indole-building-block, name is Ethyl 6-cyano-1H-indole-2-carboxylate, and the molecular formula is C12H10N2O2, Quality Control of 104291-81-8.

Sall, Daniel J. published the artcileUse of Conformationally Restricted Benzamidines as Arginine Surrogates in the Design of Platelet GPIIb-IIIa Receptor Antagonists, Quality Control of 104291-81-8, the main research area is bicyclic amidine preparation platelet receptor antagonist; glycoprotein platelet receptor antagonist bicyclic amidine.

The use of 5,6-bicyclic amidines, e.g., I, as arginine surrogates in the design of a novel class of potent platelet glycoprotein IIb-IIIa receptor antagonists is described. The addnl. conformational restriction offered by the bicyclic nucleus results in 20-400-fold increases in potency compared to the freely flexible, acyclic benzamidine counterpart. The design, synthesis, structure-activity relationships (SAR), and in vitro activity of this novel class of GPIIb-IIIa antagonists are presented.

Koenig, Stefan G.’s team published research in ACS Sustainable Chemistry & Engineering in 2014-06-02 | CAS: 104291-81-8

ACS Sustainable Chemistry & Engineering published new progress about Cross-coupling reaction. 104291-81-8 belongs to class indole-building-block, name is Ethyl 6-cyano-1H-indole-2-carboxylate, and the molecular formula is C12H10N2O2, Recommanded Product: Ethyl 6-cyano-1H-indole-2-carboxylate.

Koenig, Stefan G. published the artcileCopper-Catalyzed Synthesis of Indoles and Related Heterocycles in Renewable Solvents, Recommanded Product: Ethyl 6-cyano-1H-indole-2-carboxylate, the main research area is copper catalyst cross coupling acetamidoacetate bromobenzaldehyde renewable solvent; indolecarboxylate preparation green chem; fused heterocycle preparation green chem.

An efficient one-pot cascade to indoles and related fused heterocycles has been demonstrated in renewable solvents (EtOAc, 2-methyltetrahydrofuran), thereby eliminating the previously required dipolar aprotic solvent. The copper-catalyzed reaction proceeds with a range of bromobenzaldehydes to give products in good yields. E.g., in presence of CuI and Cs2CO3 under nitrogen in EtOAc, cross-coupling of 2-BrC6H4CHO and Et acetamidoacetate gave 59% indole derivative (I). In addition, the external ligand-free cross-coupling methodol. provides convenient access to an investigational treatment for central nervous system disorders.

Williams, John D.’s team published research in Bioorganic & Medicinal Chemistry in 2013-12-15 | CAS: 104291-81-8

Bioorganic & Medicinal Chemistry published new progress about Antibacterial agents. 104291-81-8 belongs to class indole-building-block, name is Ethyl 6-cyano-1H-indole-2-carboxylate, and the molecular formula is C12H10N2O2, Recommanded Product: Ethyl 6-cyano-1H-indole-2-carboxylate.

Williams, John D. published the artcilePotent and broad-spectrum antibacterial activity of indole-based bisamidine antibiotics: Synthesis and SAR of novel analogs of MBX 1066 and MBX 1090, Recommanded Product: Ethyl 6-cyano-1H-indole-2-carboxylate, the main research area is indole bisamidine preparation antibacterial antibiotic; Amidine; Antibacterial; Antibiotic; Broad-spectrum; Cadogan–Sundberg reaction; Imidazoline; Indole; McMurry reductive homocoupling reaction; Reissert indole synthesis; Tetrahydropyrimidine.

The prevalence of drug-resistant bacteria in the clinic has propelled a concerted effort to find new classes of antibiotics that will circumvent current modes of resistance. The authors have previously described a set of bisamidine antibiotics that contains a core composed of two indoles and a central linker. The first compounds of the series, MBX 1066 and MBX 1090, have potent antibacterial properties against a wide range of Gram-pos. and Gram-neg. bacteria. The authors have conducted a systematic exploration of the amidine functionalities, the central linker, and substituents at the indole 3-position to determine the factors involved in potent antibacterial activity. Some of the newly synthesized compounds have even more potent and broad-spectrum activity than MBX 1066 and MBX 1090.

Lazo, John S.’s team published research in Bioorganic & Medicinal Chemistry in 2006-08-15 | CAS: 104291-81-8

Bioorganic & Medicinal Chemistry published new progress about Enzyme functional sites, active. 104291-81-8 belongs to class indole-building-block, name is Ethyl 6-cyano-1H-indole-2-carboxylate, and the molecular formula is C12H10N2O2, Recommanded Product: Ethyl 6-cyano-1H-indole-2-carboxylate.

Lazo, John S. published the artcileNovel benzofuran inhibitors of human mitogen-activated protein kinase phosphatase-1, Recommanded Product: Ethyl 6-cyano-1H-indole-2-carboxylate, the main research area is benzofuran preparation mitogen activated protein kinase phosphatase inhibition SAR.

Protein tyrosine phosphatases have a central role in the maintenance of normal cellular functionality. For example, PTP1B has been implicated in insulin-resistance, obesity, and neoplasia. Mitogen-activated protein kinase phosphatase-1 (MKP-1 or DUSP1) dephosphorylates and inactivates mitogen-activated protein kinase (MAPK) substrates, such as p38, JNK, and Erk, and has been implicated in neoplasia. The lack of readily available selective small mol. inhibitors of MKP family members has severely limited interrogation of their biol. role. Inspired by a previously identified inhibitor, NSC 357756 (I) of MKP-3, we synthesized seven NSC 357756 congeners, which were evaluated for in vitro inhibition against several protein phosphatases. Remarkably, none displayed potent inhibition against MKP-3, including the desamino NSC 357756 analog NU-154. Interestingly, NU-154 inhibited human PTP1B in vitro with an IC50 value of 24 ± 1 μM and showed little inhibition against Cdc25B, MKP-1, and VHR phosphatases. NU-126 [2-((E)-2-(5-cyanobenzofuran-2-yl)vinyl)-1H-indole-6-carbonitrile] inhibited MKP-1 and VHR in vitro but was less active against human MKP-3, Cdc25B, and PTP1B. The inhibition of MKP-1 by NU-126 was independent of redox processes. The benzofuran substructure represents a new potential scaffold for further analog development and provides encouragement that more selective and potent inhibitors of MKP family members may be achievable.

Koenig, Stefan G.’s team published research in Tetrahedron Letters in 2010-12-15 | CAS: 104291-81-8

Tetrahedron Letters published new progress about Amino esters Role: RCT (Reactant), RACT (Reactant or Reagent) (amido-). 104291-81-8 belongs to class indole-building-block, name is Ethyl 6-cyano-1H-indole-2-carboxylate, and the molecular formula is C12H10N2O2, Formula: C12H10N2O2.

Koenig, Stefan G. published the artcileA ligand-free, copper-catalyzed cascade sequence to indole-2-carboxylic esters, Formula: C12H10N2O2, the main research area is indole carboxylic ester preparation ligand free substituent effect; haloaryl aldehyde glycine amido ester heterocyclization copper catalyst.

A variety of indole-2-carboxylic esters, e.g. I, are accessible in yields up to 61% through a ligand-free, copper-catalyzed reaction of a series of com. available 2-halo aryl aldehydes with benign glycine amidoesters, including the common reagent Et acetamidoacetate. This one-pot, three-reaction format allows ready entry to the desired heterocycles from starting substrates in the reactivity order of iodo > bromo ≥ chloro substituents. An assortment of functional groups is tolerated, adding to the generality of this methodol.