Tag: M.W=200-250

Butini, Stefania published the artcileDiscovery of a New Class of Potential Multifunctional Atypical Antipsychotic Agents Targeting Dopamine D₃ and Serotonin 5-HT_1A and 5-HT_2A Receptors: Design, Synthesis, and Effects on Behavior, COA of Formula: C12H13NO3, the publication is Journal of Medicinal Chemistry (2009), 52(1), 151-169, database is CAplus and MEDLINE.

Dopamine D₃ antagonism combined with serotonin 5-HT_1A and 5-HT_2A receptor occupancy may represent a novel paradigm for developing innovative antipsychotics. The unique pharmacol. features of 5i are a high affinity for dopamine D₃, serotonin 5-HT_1A and 5-HT_2A receptors, together with a low affinity for dopamine D₂ receptors (to minimize extrapyramidal side effects), serotonin 5-HT_2C receptors (to reduce the risk of obesity under chronic treatment), and for hERG channels (to reduce incidence of torsade des pointes). Pharmacol. and biochem. data, including specific c-fos expression in mesocorticolimbic areas, confirmed an atypical antipsychotic profile of 5i in vivo, characterized by the absence of catalepsy at antipsychotic dose.

Journal of Medicinal Chemistry published new progress about 20538-12-9. 20538-12-9 belongs to indole-building-block, auxiliary class Indole,Ester,Ether, name is Ethyl 7-methoxy-1H-indole-2-carboxylate, and the molecular formula is C12H13NO3, COA of Formula: C12H13NO3.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Labre, Flavien published the artcileApplication of cooperative iron/copper catalysis to a palladium-free borylation of aryl bromides with pinacolborane, Product Details of C14H18BNO2, the publication is Organic Letters (2014), 16(9), 2366-2369, database is CAplus and MEDLINE.

A new cooperative copper/iron catalysis, comprising CuI/Fe(acac)₃ mixtures modified with diamines, provides facile access to arylboronates ArBpin bromine for boron substitution in reaction of ArBr with HBpin at -10°. Use of the toxic, precious metal Pd is avoided. The mechanisms of the borylation and protodebromination side reaction, giving arenes ArH, are discussed on the basis of calculated potential energy surfaces.

Organic Letters published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H18BNO2, Product Details of C14H18BNO2.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Tani, Masanobu published the artcileSynthetic studies on indoles and related compounds. Part 40. Regioselective and non-reductive C(3)-debromination of indole nucleus, Category: indole-building-block, the publication is Synlett (1996), 931-932, database is CAplus.

A method of debromination of 3-bromoindoles was developed. Various 3-bromoindole-2-carboxylates were treated with H₂SO₄ and LiBr in AcOH to give the corresponding C(3)-debrominated indoles in excellent yields. The same reaction with 3-bromo-N-tosylindoles gave lower yields.

Synlett published new progress about 20538-12-9. 20538-12-9 belongs to indole-building-block, auxiliary class Indole,Ester,Ether, name is Ethyl 7-methoxy-1H-indole-2-carboxylate, and the molecular formula is C10H15ClO3S, Category: indole-building-block.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Nycholat, Corwin M. published the artcileA sulfonamide sialoside analogue for targeting Siglec-8 and -F on immune cells, Synthetic Route of 166883-20-1, the publication is Journal of the American Chemical Society (2019), 141(36), 14032-14037, database is CAplus and MEDLINE.

The Siglec family of cell surface receptors have emerged as attractive targets for cell-directed therapies due to their restricted expression on immune cells, endocytic properties, and ability to modulate receptor signaling. Human Siglec-8, for instance, has been identified as a therapeutic target for the treatment of eosinophil and mast cell disorders. A promising strategy to target Siglecs involves the use of liposomal nanoparticles with a multivalent display of Siglec ligands. A key challenge for this approach is the identification of a high affinity ligand for the target Siglec. Here, we report the development of a ligand of Siglec-8 and its closest murine functional orthologue Siglec-F that is capable of targeting liposomes to cells expressing Siglec-8 or -F. A glycan microarray library of synthetic 9-N-sulfonyl sialoside analogs was screened to identify potential lead compounds The best ligand, 9-N-(2-naphthyl-sulfonyl)-Neu5Acα2-3-[6-O-sulfo]-Galβ1-4GlcNAc (6′-O-sulfo ^NSANeu5Ac) combined the lead 2-naphthyl sulfonyl C-9 substituent with the preferred sulfated scaffold. The ligand 6′-O-sulfo ^NSANeu5Ac was conjugated to lipids for display on liposomes to evaluate targeted delivery to cells. Targeted liposomes showed strong in vitro binding/uptake and selectivity to cells expressing Siglec-8 or -F and, when administered to mice, exhibit in vivo targeting to Siglec-F⁺ eosinophils.

Journal of the American Chemical Society published new progress about 166883-20-1. 166883-20-1 belongs to indole-building-block, auxiliary class Indoline,Chloride,Sulfonyl chlorides,Amide, name is 1-Methyl-2-oxoindoline-5-sulfonyl chloride, and the molecular formula is C9H8ClNO3S, Synthetic Route of 166883-20-1.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Taylor, Nicholas J. published the artcileDerisking the Cu-Mediated ¹⁸F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands, Related Products of indole-building-block, the publication is Journal of the American Chemical Society (2017), 139(24), 8267-8276, database is CAplus and MEDLINE.

The compatibility of various heterocycles, particularly nitrogen heterocycles, towards the copper-mediated ¹⁸F-fluorination of aryl pinacolboronates with ¹⁸F-fluoride was determined using fluorination reactions of a model substrate in the presence of exogenous heterocycles and the fluorination reactions of substrates possessing heterocycles with fluorination on an attached aromatic ring or directly attached to the heterocycle of interest. Using this information, syntheses of seven ¹⁸F-labeled structurally complex pharmaceutically relevant heterocycle-containing mols. were designed and executed. The method may be useful in designing syntheses of other radiolabeled compounds and delineating the scope of utility of other radiolabeling methods.

Journal of the American Chemical Society published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C23H43NP2, Related Products of indole-building-block.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Sanz, Roberto published the artcileDioxomolybdenum(VI)-catalyzed reductive cyclization of nitroaromatics. Synthesis of carbazoles and indoles, Category: indole-building-block, the publication is Advanced Synthesis & Catalysis (2007), 349(4+5), 713-718, database is CAplus.

Reductive cyclization of nitrobiphenyls and nitrostyrenes to carbazoles and indoles, resp., is carried out by triphenylphosphine under mild conditions catalyzed by a dichlorodioxomolybdenum(VI) complex. A one-pot procedure for the synthesis of regioselectively functionalized indoles has been developed from com. available o-nitrobenzaldehydes and phosphoranes.

Advanced Synthesis & Catalysis published new progress about 20538-12-9. 20538-12-9 belongs to indole-building-block, auxiliary class Indole,Ester,Ether, name is Ethyl 7-methoxy-1H-indole-2-carboxylate, and the molecular formula is C12H13NO3, Category: indole-building-block.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Hoffman, A. published the artcileThe structure and synthesis of psilocybin, Name: Ethyl 7-methoxy-1H-indole-2-carboxylate, the publication is Experientia (1958), 397-9, database is CAplus.

Psilocybin, the psychotropic active principle from Psilocybe mexicana, was found to be the H₃PO₄ ester of 4-hydroxydimethyltryptamine (I). Hydrolysis of I gave 4-hydroxydimethyltryptamine which was synthesized from 4-benzyloxyindole by the oxalyl chloride method (Speeter, et al., C.A. 49, 15852f).

Experientia published new progress about 20538-12-9. 20538-12-9 belongs to indole-building-block, auxiliary class Indole,Ester,Ether, name is Ethyl 7-methoxy-1H-indole-2-carboxylate, and the molecular formula is C12H13NO3, Name: Ethyl 7-methoxy-1H-indole-2-carboxylate.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Blomgren, Peter published the artcileDiscovery of Lanraplenib (GS-9876): A Once-Daily Spleen Tyrosine Kinase Inhibitor for Autoimmune Diseases, Product Details of C14H18BNO2, the publication is ACS Medicinal Chemistry Letters (2020), 11(4), 506-513, database is CAplus and MEDLINE.

Spleen tyrosine kinase (SYK) is a critical regulator of signaling in a variety of immune cell types such as B-cells, monocytes, and macrophages. Accordingly, there have been numerous efforts to identify compounds that selectively inhibit SYK as a means to treat autoimmune and inflammatory diseases. We previously disclosed GS-9973 (entospletinib) as a selective SYK inhibitor that is under clin. evaluation in hematol. malignancies. However, a BID dosing regimen and drug interaction with proton pump inhibitors (PPI) prevented development of entospletinib in inflammatory diseases. Herein, we report the discovery of a second-generation SYK inhibitor, GS-9876 (lanraplenib), which has human pharmacokinetic properties suitable for once-daily administration and is devoid of any interactions with PPI. Lanraplenib is currently under clin. evaluation in multiple autoimmune indications.

ACS Medicinal Chemistry Letters published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H18BNO2, Product Details of C14H18BNO2.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Hieda, Yuhzo published the artcileTotal Synthesis of the Neuronal Cell-Protecting Carbazole Alkaloids Carbazomadurin A and (S)-(+)-Carbazomadurin B, COA of Formula: C12H13NO3, the publication is European Journal of Organic Chemistry (2013), 2013(32), 7391-7401, database is CAplus.

The total syntheses of the neuronal cell-protecting carbazole alkaloids carbazomadurin A and (S)-(+)-carbazomadurin B, I [R = Me, (S)-Et, resp.], were achieved. The key step of the synthesis of the polysubstituted carbazole rings included an allene-mediated electrocyclic reaction of the 6π-electron system that involved the indole 2,3-bond. The cleavage of the alkoxy groups of the resulting 3-ethoxy-8-isopropoxycarbazole successfully gave the 3,8-dihydroxycarbazole, which was converted into the 3,8-bis(OSEM)-carbazole (SEM = 2-trimethylsilylethoxymethyl). A Suzuki-Miyaura cross-coupling reaction of the 3,8-bis(OSEM)-carbazole with the corresponding alkenyl pinacol borates afforded the 1-alkenylcarbazoles, which were treated with tetra-n-butylammonium fluoride (TBAF) followed by reduction with NaBH₄ to provide carbazomadurin A and (S)-(+)-carbazomadurin B, resp.

European Journal of Organic Chemistry published new progress about 20538-12-9. 20538-12-9 belongs to indole-building-block, auxiliary class Indole,Ester,Ether, name is Ethyl 7-methoxy-1H-indole-2-carboxylate, and the molecular formula is C12H13NO3, COA of Formula: C12H13NO3.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Jin, Shengfei published the artcileVisible Light-Induced Borylation of C-O, C-N, and C-X Bonds, Name: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, the publication is Journal of the American Chemical Society (2020), 142(3), 1603-1613, database is CAplus and MEDLINE.

Aryl phosphates, arylammonium salts and aryl halides were borylated with B₂pin₂ in photochem. substitution reaction catalyzed by phenothiazines, yielding aryl pinacolboranes and aryltrifluoroborates. Boronic acids are centrally important functional motifs and synthetic precursors. Visible light-induced borylation may provide access to structurally diverse boronates, but a broadly efficient photocatalytic borylation method that can effect borylation of a wide range of substrates, including strong C-O bonds, remains elusive. Herein, we report a general, metal-free visible light-induced photocatalytic borylation platform that enables borylation of electron-rich derivatives of phenols and anilines, chloroarenes, as well as other haloarenes. The reaction exhibits excellent functional group tolerance, as demonstrated by the borylation of a range of structurally complex substrates. Remarkably, the reaction is catalyzed by phenothiazine, a simple organic photocatalyst with MW < 200 that mediates the previously unachievable visible light-induced single electron reduction of phenol derivatives with reduction potentials as neg. as approx. – 3 V vs. SCE by a proton-coupled electron transfer mechanism. Mechanistic studies point to the crucial role of the photocatalyst-base interaction.

Journal of the American Chemical Society published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H18BNO2, Name: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles