177167-52-1

Upstream product

• 942069-73-0 2-(3,5-dichloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 7149-69-1 1,3-dichloro-2-methyl-5-nitrobenzene 
• 99-99-0 1-methyl-4-nitrobenzene 
• 3032-81-3 3,5-dichloroiodobenzene 
• 77-78-1 dimethyl sulfate 
• 54730-35-7 3,5-dichloro-4-methylaniline 

Downstream Products

• 39652-34-1 3,5-dichloro-4-methylbenzoic acid 
• 942069-73-0 2-(3,5-dichloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1432445-09-4 1,3-dichloro-2-methyl-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene 
• 1437779-31-1 5-(5-(3,5-dichloro-4-methylphenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol 
• 177167-51-0 2,6-dichloro-4-iodobenzyl acetate 
• 177167-62-3 2,6-dichloro-4-<(trimethylsilyl)ethynyl>benzaldehyde 
• 177167-61-2 (2,6-dichloro-4-iodophenyl)methanol 
• 177167-53-2 2,6-dichloro-4-iodobenzaldehyde 
• 177167-50-9 5-iodo-2-(bromomethyl)-1,3-dichlorobenzene 

Relevant academic research and scientific papers

Fragment-based lead discovery of a novel class of small molecule antagonists of neuropeptide B/W receptor subtype 1 (GPR7)

Here, we report the discovery of a new class of NPBWR1 antagonists identified from a fragment-based screen. Compound 1 (cAMP IC50 = 250 μM; LE = 0.29) emerged as an initial hit. Further optimization of 1 by SAR-by-catalogue and chemical modification produced 21a (cAMP IC50 = 30 nM; LE = 0.39) with a 6700-fold increase in potency from fragment 1. Somewhat surprisingly, Schild analysis of compound 21a suggested that in vitro inhibition of NPW-mediated effects on upon cAMP accumulation were saturable, and that compound 21a dose-dependently increased [125I]-hNPW23 dissociation rate constants from NPBWR1 in kinetic binding studies. Collectively, these data are inconsistent with a classic surmountable, orthosteric mechanism of inhibition. The benzimidazole inhibitors reported herein may therefore represent a mechanistically differentiated class of compounds with which to form a better appreciation of the pharmacology and physiological roles of this central neuropeptide system.

BORON-CONTAINING SMALL MOLECULES

This invention provides novel compounds, methods of using the compounds, and pharmaceutical formulations comprising the compounds.

Sterically controlled iodination of arenes via iridium-catalyzed C-H borylation

A mild method to prepare aryl and heteroaryl iodides by sequential C-H borylation and iodination is reported. The regioselectivity of this process is controlled by steric effects on the C-H borylation step and is complementary to existing methods to form aryl iodides. The iodination of boronic esters has potential for the synthesis of radiolabeled aryl iodides, as demonstrated by the concise synthesis of a potential tracer for SPECT imaging.

Proton mobility in 2-substituted 1,3-dichlorobenzenes: "ortho" or "meta" metalation?

Nine 1,3-dichlorobenzene congeners were selected as model compounds to assess the relative rates of proton abstraction from 4- and 5-positions ("ortho" vs. "meta" metalation). Using lithium 2,2,6,6-tetramethylpiperidide as the basic reagent, the chlorine-adjacent 4-position underwent metalation exclusively. In contrast, attack at the chlorine-remote 5-posi" tion became significant even in the case of moderately sized 2-substituents (such as dimethylamino or ethyl) when secbutyllithium was employed. The "ortho/para" (4-/5-) ratios ranged from 80:20 to 65:35. The more pronounced "meta-orienting" effect of silicon as opposed to carbon substituents can be attributed to dissimilarities in the n polarization of the aromatic ring. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Synthesis of regiospecifically meso-functionalized tetraarylporphyrins via arylbis(2-pyrrolyl)methanes

This paper describes the synthesis of three new porphyrins 1-3 of alternate A2B2 structure, by condensation of arylbis(2-pyrrolyl)methanes and arylaldehydes bearing suitable reactive substituents for further synthetic manipulations. This synthetic approach allows to place the reactive groups selectively on the 5,15 meso-aryls. The new porphyrins feature an ortho-nitro group in the case of 1 and a protected paraethynyl group in compounds 2 and 3. Porphyrin l, after reduction of the nitro group, is a useful intermediate for the preparation of cage or regiospecifically bis-tailed porphyrins. Compounds 2 and 3, after deprotection and Glaser-Hay coupling should give linear polymers (molecular wires) suitable for electron-transfer and light-harvesting processes.