51688-72-3

Upstream product

• 643-28-7 2-isopropylaniline 
• 108-24-7 acetic anhydride 
• 81090-34-8 4-bromo-2-isopropyl-aniline 
• 64-19-7 acetic acid 
• 19246-04-9 N-(2-isopropylphenyl)acetamide 

Downstream Products

• 1079742-87-2 4-bromo-N-ethyl-2-isopropylaniline 
• 1079742-88-3 4-bromo-N,N-diethyl-2-isopropylaniline 
• 1079742-89-4 4-(diethylamino)-3-isopropylbenzaldehyde 
• 1427716-68-4 (E,E)-2,5-bis[2-(3-isopropyl-4-N,N-diethylaminophenyl)ethenyl]pyrazine 
• 51688-76-7 4-amino-3-isopropylbenzoic acid 
• 51688-74-5 N-(4-cyano-2-isopropylphenyl)acetamide 

Relevant academic research and scientific papers

Hit-to-Lead Optimization of Mouse Trace Amine Associated Receptor 1 (mTAAR1) Agonists with a Diphenylmethane-Scaffold: Design, Synthesis, and Biological Study

The trace amine-associated receptor 1 (TAAR1) is a G-protein-coupled receptors (GPCR) potently activated by a variety of molecules besides trace amines (TAs), including thyroid hormone-derivatives like 3-iodothyronamine (T1AM), catechol-O-methyltransferase products like 3-methoxytyramine, and amphetamine-related compounds. Accordingly, TAAR1 is considered a promising target for medicinal development. To gain more insights into TAAR1 physiological functions and validation of its therapeutic potential, we recently developed a new class of thyronamine-like derivatives. Among them compound SG2 showed high affinity and potent agonist activity at mouse TAAR1. In the present work, we describe design, synthesis, and SAR study of a new series of compounds (1-16) obtained by introducing specific structural changes at key points of our lead compound SG2 skeleton. Five of the newly synthesized compounds displayed mTAAR1 agonist activity higher than both SG2 and T1AM. Selected diphenylmethane analogues, namely 1 and 2, showed potent functional activity in in vitro and in vivo models.

Positron Emission Tomography Imaging of Neurotensin Receptor-Positive Tumors with68Ga-Labeled Antagonists: The Chelate Makes the Difference Again

Neurotensin receptor 1 (NTS1) is involved in the development and progression of numerous cancers, which makes it an interesting target for the development of diagnostic and therapeutic agents. A small molecule NTS1antagonist, named [

Design, synthesis and biological evaluation of novel TRβ selective agonists sustained by ADME-toxicity analysis

Although triiodothyronine (T3) induces several beneficial effects on lipid metabolism, its use is hampered by toxic side-effects, such as tachycardia, arrhythmia, heart failure, bone and muscle catabolism and mood disturbances. Since the α isoform of thyroid hormone receptors (TRs) is the main cause of T3-related harmful effects, several efforts have been made to develop selective agonists of the β isoform that could induce some beneficial effects (i.e. lowering triglyceride and cholesterol levels reducing obesity and improving metabolic syndrome), while overcoming most of the adverse T3-dependent side effects. Herein, we describe the drug discovery process sustained by ADME-Toxicity analysis that led us to identify novel agonists with selectivity for the isoform TRβ and an acceptable off-target and absorption, distribution metabolism, excretion and toxicity (ADME-Tox) profile. Within the small series of compounds synthesized, derivatives 1 and 3, emerge from this analysis as “potentially safe” to be engaged in preclinical studies. In in vitro investigation proved that both compounds were able to reduce lipid accumulation in HepG2 and promote lipolysis with comparable effects to those elicited by T3, used as reference drug. Moreover, a preliminary in vivo study confirmed the apparent lack of toxicity, thus suggesting compounds 1 and 3 as new potential TRβ-selective thyromimetics.

NOVEL THYROMIMETICS WITH A BIPHENYLMETHANE SCAFFOLD AND THEIR USE

The invention concerns a compound of Formula (I) or a salt thereof, wherein R1 is H, (C1-C3)alkyl or CF3; R2 is H, (C1-C3)alkyl or CF3; A is CH2COOH, XCH2COOCH2CH3, XCH2COOH, XCH2CH2NH2, where X is nitrogen or oxygen atom; Ar is an aromatic fragment selected from the group consisting of (Ar1), (Ar2) and (Ar3); where R3 is H, -CH3, -CH2CH3 or CH3CO-, R4 is H or -CH3, R5 is H or -CH3, and R6 is H or -CH3. The compounds of Formula (I) can be used in the treatment of diseases modulated by thyroid hormone receptor-beta (TRb or TRβ).

Flow-Assisted Synthesis: A Key Fragment of SR 142948A

We report a series of multi-step flow operations to deliver an advanced hydrazine intermediate used in the assembly of the neurotensin modulator SR 142948A. Several new reactor configurations have enabled chemical transformations that would be otherwise difficult or dangerous to perform at scale. Overall the flow approach has allowed the preparation of kilogram quantities of the required hydrazine through a short and efficient route.

Donor-substituted distyrylpyrazines: Influence of steric congestion on UV-Vis absorption and fluorescence

Di(p-aminostyryl)pyrazines with voluminous substituents on the nitrogen and in the adjacent positions were prepared via twofold aldol condensation. Absorption and emission spectra are influenced by increasing steric hindrance because the orbital overlap between nitrogen and π-system is modulated by voluminous groups. Strong solvatochromism of the fluorescence and huge Stokes shifts result from amplified donor-acceptor interaction in the excited state. Protonation occurs at the terminal amino groups first, followed by protonation of the central pyrazine. With increasing strength of acid, absorption and emission spectra are first shifted to the blue followed by a redshift. Copyright

Novel Phosphinic Acid-Containing Thyromimetics

The present invention relates to compounds of phosphonic acid-containing T3 mimetics and monoesters thereof, stereoisomers, pharmaceutically acceptable salts, co-crystals, and prodrugs thereof and pharmaceutically acceptable salts and co-crystals of the prodrugs, as well as their preparation and uses for preventing and/or treating metabolic diseases such as obesity, NASH, hypercholesterolemia and hyperlipidemia, as well as associated conditions such as atherosclerosis, coronary heart disease, impaired glucose tolerance, metabolic syndrome x and diabetes.

NOVEL PHOSPHORUS-CONTAINING THYROMIMETICS

The present invention relates to compounds of phosphonic acid containing T3 mimetics, stereoisomers, pharmaceutically acceptable salts, co-crystals, and prodrugs thereof and pharmaceutically acceptable salts and co-crystals of the prodrugs, as well as their preparation and uses for preventing and/or treating metabolic diseases such as obesity, NASH, hypercholesterolemia and hyperlipidemia, as well as associated conditions such as atherosclerosis, coronary heart disease, impaired glucose tolerance, metabolic syndromex and diabetes.

Substituted 1-phenyl-3-pyrazolecarboxamides active on neurotensin receptors, their preparation and pharmaceutical compositions containing them

The invention relates to new substituted 1-phenyl-3-pyrazolecarboxamides having a great affinity for human neurotensin receptors, to a process for preparing them and to pharmaceutical compositions containing them as active principles. More particularly, this invention relates to the discovery that the affinity for neurotensin receptors, especially human neurotensin receptors, is increased by substituting the phenyl group of 1-phenyl-3-pyrazolecarboxamide compounds with particular groups.