92057-12-0

Basic information

• Product Name: 3-(2-THIENYL)ANILINE
• Synonyms: ART-CHEM-BB B025012;3-THIOPHEN-2-YL-PHENYLAMINE;AKOS BAR-0199;AKOS B025012;3-(2-THIENYL)ANILINE;3-(2-THIENYL)ANILINE HYDROCHLORIDE;3-(Thien-2-yl)aniline hydrochloride;3-(thiophen-2-yl)aniline
• CAS NO: 92057-12-0
• Molecular Formula: C₁₀H₉NS
• Molecular Weight: 175.25
• Mol File: 92057-12-0.mol

Chemical Properties

• Melting Point: 246 °C
• Boiling Point: 341.6 °C at 760 mmHg
• Flash Point: 160.4 °C
• Appearance: /
• Density: 1.196 g/cm³
• Vapor Pressure: 7.98E-05mmHg at 25°C
• Refractive Index: 1.65
• PKA: 4.09±0.10(Predicted)
• CAS DataBase Reference: 3-(2-THIENYL)ANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-THIENYL)ANILINE(92057-12-0)
• EPA Substance Registry System: 3-(2-THIENYL)ANILINE(92057-12-0)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25
• Safety Statements: 45
• Hazardous Substances Data: 92057-12-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(2-Thienyl)aniline is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to form stable complexes with biological targets, making it a valuable building block for the development of new drugs.
Used in Chemical Research:
3-(2-Thienyl)aniline is used as a reagent in palladium-catalyzed Suzuki-Miyaura cross-couplings, a widely used method for the formation of carbon-carbon bonds in organic synthesis. Its presence in these reactions can enhance the efficiency and selectivity of the process.
Used in Material Science:
3-(2-Thienyl)aniline is used in the preparation of photophysical properties of oxygen-containing polycyclic aromatic triptycenes. These materials exhibit unique optical and electronic properties, making them promising candidates for applications in optoelectronics, photovoltaics, and other advanced technologies.

InChI:InChI=1/C10H9NS/c11-9-4-1-3-8(7-9)10-5-2-6-12-10/h1-7H,11H2

Upstream product

• 38178-61-9 2‐(3‐nitrophenyl)thiophene 
• 13331-27-6 m-nitrobenzene boronic acid 
• 6165-68-0 thiophene boronic acid 
• 591-19-5 m-Bromoaniline 
• 585-79-5 m-nitrobromobenzene 
• 586-78-7 para-nitrophenyl bromide 
• 1003-09-4 2-bromothiophene 
• 30418-59-8 3-Aminophenylboronic acid 

Downstream Products

• 849235-28-5 4-[(3,4-dimethoxy-phenylamino)-methyl]-N-(3-thiophen-2-yl-phenyl)-benzamide 
• 1415022-41-1 C₁₂H₉Cl₂NOS 

Relevant articles and documents

Discovery, optimization and evaluation of 1-(indolin-1-yl)ethan-1-ones as novel selective TRIM24/BRPF1 bromodomain inhibitors

TRIM24 (tripartite motif-containing protein 24) and BRPF1 (bromodomain and PHD finger containing protein 1) are epigenetics “readers” and potential therapeutic targets for cancer and other diseases. Here we describe the structure-guided design of 1-(indolin-1-yl)ethan-1-ones as novel TRIM24/BRPF1 bromodomain inhibitors. The representative compound 20l (Y08624) is a new TRIM24/BRPF1 dual inhibitor, with IC50 values of 0.98 and 1.16 μM, respectively. Cellular activity of 20l was validated by viability assay in prostate cancer (PC) cell lines. In PC xenograft models, 20l suppressed tumor growth (50 mg/kg/day, TGI = 53%) without exhibiting noticeable toxicity. Compound 20l represents a versatile starting point for the development of more potent TRIM24/BRPF1 inhibitors.

Chemical validation of a druggable site on Hsp27/HSPB1 using in silico solvent mapping and biophysical methods

Destabilizing mutations in small heat shock proteins (sHsps) are linked to multiple diseases; however, sHsps are conformationally dynamic, lack enzymatic function and have no endogenous chemical ligands. These factors render sHsps as classically “undruggable” targets and make it particularly challenging to identify molecules that might bind and stabilize them. To explore potential solutions, we designed a multi-pronged screening workflow involving a combination of computational and biophysical ligand-discovery platforms. Using the core domain of the sHsp family member Hsp27/HSPB1 (Hsp27c) as a target, we applied mixed solvent molecular dynamics (MixMD) to predict three possible binding sites, which we confirmed using NMR-based solvent mapping. Using this knowledge, we then used NMR spectroscopy to carry out a fragment-based drug discovery (FBDD) screen, ultimately identifying two fragments that bind to one of these sites. A medicinal chemistry effort improved the affinity of one fragment by ~50-fold (16 μM), while maintaining good ligand efficiency (~0.32 kcal/mol/non-hydrogen atom). Finally, we found that binding to this site partially restored the stability of disease-associated Hsp27 variants, in a redox-dependent manner. Together, these experiments suggest a new and unexpected binding site on Hsp27, which might be exploited to build chemical probes.

COMPOUNDS AND METHODS TO ATTENUATE TUMOR PROGRESSION AND METASTASIS

This invention relates to certain compounds or pharmaceutically acceptable salts thereof, and for the use of the compounds to treat cancer. In another aspect, the disclosure relates to a pharmaceutical composition comprising a compound of Formula (1), For

Small-Molecule Covalent Modification of Conserved Cysteine Leads to Allosteric Inhibition of the TEAD?Yap Protein-Protein Interaction

The Hippo pathway coordinates extracellular signals onto the control of tissue homeostasis and organ size. Hippo signaling primarily regulates the ability of Yap1 to bind and co-activate TEA domain (TEAD) transcription factors. Yap1 tightly binds to TEAD4

Diarylureas Containing 5-Membered Heterocycles as CB1 Receptor Allosteric Modulators: Design, Synthesis, and Pharmacological Evaluation

Allosteric modulators have attracted significant interest as an alternate strategy to modulate CB1 receptor signaling for therapeutic benefits that may avoid the adverse effects associated with orthosteric ligands. Here we extended our previous structure-activity relationship studies on the diarylurea-based CB1 negative allosteric modulators (NAMs) by introducing five-membered heterocycles to replace the 5-pyrrolidinylpyridinyl group in PSNCBAM-1 (1), one of the first generation CB1 allosteric modulators. Many of these compounds had comparable potency to 1 in blocking the CB1 agonist CP55,940 stimulated calcium mobilization and [35S]GTP-γ-S binding. Similar to 1, most compounds showed positive cooperativity by increasing [3H]CP55,940 binding, consistent with the positive allosteric modulator (PAM)-antagonist mechanism. Interestingly, these compounds exhibited differences in ability to increase specific binding of [3H]CP55,940 and decrease binding of the antagonist [3H]SR141716. In saturation binding studies, only increases in [3H]CP55,940 Bmax, but not Kd, were observed, suggesting that these compounds stabilize low affinity receptors into a high affinity state. Among the series, the 2-pyrrolyl analogue (13) exhibited greater potency than 1 in the [35S]GTP-γ-S binding assay and significantly enhanced the maximum binding level in the [3H]CP5,5940 binding assay, indicating greater CB1 receptor affinity and/or cooperativity.

DIARYLUREAS AS CB1 ALLOSTERIC MODULATORS

The present invention provides novel diarylurea derivatives (compounds of formula (I)) and their uses. The compounds of the present invention are demonstrated to be allosteric modulators of the CB1 receptor, and therefore useful for the treatment of diseases and conditions mediated by CB1.

Design, synthesis and biological evaluation of N-arylphenyl-2,2- dichloroacetamide analogues as anti-cancer agents

Our earlier research has shown that N-phenyl-2,2-dichloroacetamide analogues had much higher anti-cancer activity than the lead compound sodium dichloroacetate (DCA). In this current study, a variety of N-arylphenyl-2,2- dichloroacetamide analogues were synthesized via Suzuki coupling reaction and their anti-cancer activity was evaluated. The results showed that N-terphenyl-2,2-dichloroacetamide analogues had satisfactory anti-cancer activity. Among them, N-(3,5-bis(benzo[d][1,3]dioxol-5-yl)phenyl)-2,2- dichloroacetamide (6 k) had an IC50 of 2.40 μM against KB-3-1 cells, 1.04 μM against H460 cells and 1.73 μM against A549 cells.

3-AZABICYCLO [3.1.0] HEXANE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS

The present invention relates to 3-azabicyclo[3.1.0]hexane derivatives, which are useful as vanilloid receptor (VR) ligands, methods of treating diseases, conditions and/or disorders modulated by vanilloid receptors with them, and processes for preparing them.

INHIBITORS OF HISTONE DEACETYLASE

The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

Method for treating neoplasia with amino or pyridylamino cyclobutene derivatives

A method for inhibiting neoplasia, particularly cancerous and precancerous lesions by exposing the affected cells to amino or pyridylamino cyclobutane derivatives.