Category: 13682-33-2

Oh, Sangmi published the artcileIdentification of Piperidine-3-carboxamide Derivatives Inducing Senescence-like Phenotype with Antimelanoma Activities, Quality Control of 13682-33-2, the publication is ACS Medicinal Chemistry Letters (2021), 12(4), 563-571, database is CAplus and MEDLINE.

This study evaluated the potential use of senescence-inducing small mols. in the treatment of melanoma. We screened com. available small-mol. libraries with high-throughput screening and high-content screening image-based technol. Our findings showed an initial hit with the embedded N-arylpiperidine-3-carboxamide scaffold induced senescence-like phenotypic changes in human melanoma A375 cells without serious cytotoxicity against normal cells. A focused library containing diversely modified analogs were constructed and examined to evaluate the structure-activity relationship of N-arylpiperidine-3-carboxamide derivatives starting from hit 1. This work identified a novel compound with remarkable antiproliferative activity in vitro and demonstrated the key structural moieties within.

ACS Medicinal Chemistry Letters published new progress about 13682-33-2. 13682-33-2 belongs to imidazoles-derivatives, auxiliary class Imidazole,Amine,Benzene, name is 4-(1H-Imidazol-2-yl)aniline, and the molecular formula is C9H9N3, Quality Control of 13682-33-2.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Smith, Leon M. II published the artcileNovel phenylalanine derived diamides as Factor XIa inhibitors, Application In Synthesis of 13682-33-2, the publication is Bioorganic & Medicinal Chemistry Letters (2016), 26(2), 472-478, database is CAplus and MEDLINE.

The synthesis, structural activity relationships (SAR), and selectivity profile of a potent series of phenylalanine diamide FXIa inhibitors will be discussed. Exploration of P1 prime and P2 prime groups led to the discovery of compounds with high FXIa affinity, good potency in our clotting assay (aPPT), and high selectivity against a panel of relevant serine proteases as exemplified by compound (I). Compound I demonstrated good in vivo efficacy (EC₅₀ = 2.8 μM) in the rabbit elec. induced carotid arterial thrombosis model (ECAT).

Bioorganic & Medicinal Chemistry Letters published new progress about 13682-33-2. 13682-33-2 belongs to imidazoles-derivatives, auxiliary class Imidazole,Amine,Benzene, name is 4-(1H-Imidazol-2-yl)aniline, and the molecular formula is C10H9NO4S, Application In Synthesis of 13682-33-2.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Currie, Kevin S. published the artcileDiscovery of GS-9973, a Selective and Orally Efficacious Inhibitor of Spleen Tyrosine Kinase, Quality Control of 13682-33-2, the publication is Journal of Medicinal Chemistry (2014), 57(9), 3856-3873, database is CAplus and MEDLINE.

Spleen tyrosine kinase (Syk) is an attractive drug target in autoimmune, inflammatory, and oncol. disease indications. The most advanced Syk inhibitor, R406, (or its prodrug form fostamatinib), has shown efficacy in multiple therapeutic indications, but its clin. progress has been hampered by dose-limiting adverse effects that have been attributed, at least in part, to the off-target activities of R406. It is expected that a more selective Syk inhibitor would provide a greater therapeutic window. Herein the authors report the discovery and optimization of a novel series of imidazo[1,2-a]pyrazine Syk inhibitors. This work culminated in the identification of GS-9973, a highly selective and orally efficacious Syk inhibitor which is currently undergoing clin. evaluation for autoimmune and oncol. indications.

Journal of Medicinal Chemistry published new progress about 13682-33-2. 13682-33-2 belongs to imidazoles-derivatives, auxiliary class Imidazole,Amine,Benzene, name is 4-(1H-Imidazol-2-yl)aniline, and the molecular formula is C9H9N3, Quality Control of 13682-33-2.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Balaban, I. E. published the artcileTrypanocidal action and chemical constitution. III. Arsonic acids containing the glyoxaline nucleus, Safety of 4-(1H-Imidazol-2-yl)aniline, the publication is Journal of the Chemical Society, Abstracts (1925), 2801-14, database is CAplus.

Glyoxaline-4(or 5)-carboxyanilide nitrate is dimorphous, both forms crystallizing with 0.5 H₂O, unstable fluffy needles and stable, stout prisms, m. 170-1° (decomposition); gradually added to concentrated H₂SO₄ at O°, there results 36 g. of the p-nitro derivative (I), crystallizing with 2 AcOH, m. 307° (corrected), soluble in 2 N NaOH with a pale yellow color (HCl salt, crystallizing with 1 H₂O, decomposes about 298°; nitrate, m. 205° (decomposition)) and 14.3% of the o-nitro derivative, bright yellow, m. 229° (HCl salt, yellow prisms; nitrate, yellow, m. 196° (decomposition)). Reduction of I with SnCl₂ and HCl gives the p-amino derivative (II), plates, m. 228°; di-HCl salt, crystallizing with 1 H₂O, blackens about 290°; the diazo solution couples with alk. β-C₁₀H₇OH with a red color; chlorostannate, pale yellow, m. 290° (decomposition); picrate, yellow, darkens 256°, decomposes 266°, crystallizing with 1.5 H₂O. The o-amino derivative (III), m. 270°; di-HCl salt, crystallizing with 0.5 H₂O, decomposes 310°; diazoimide, m. 195-6°, produces no color with alk. β-C₁₀H₇OH; it is very sparingly soluble in H₂O and will detect HNO₂ as a solid crystalline derivative at a dilution of 1 in 6400 in the presence of AcONa, or, conversely, the anilide can be detected at a dilution of 1 in 5000. Dipicrate, crystallizing with 2.5 H₂O, m. 242° (decomposition). II, diazotized and treated with As₂O₃, gives 36% of glyoxaline-4′(or 5′)-carboxy-p-aminophenylarsonic acid, pale yellow, darkens 280°, crystallizing from 25% HCO₂H with 1 H₂O; Mg salt, fine needles; Ca salt, anisotropic spheroids; Na salt, needles; HCl salt, fine needles. Nitration at 0° gives the 3-nitro derivative, yellow plates with 1 H₂O, m. about 327° (decomposition); Mg, Ca, Ba and Li salts. Reduction with FeCl₂ in NaOH at -5° gives 86% of the 3-amino derivative, prisms, does not m. 320°; it crystallines with 0.5 H₂O, not lost at 100°. NaNO₂ in a HCl solution causes the immediate precipitation of the diazoimide, micro-leaflets, which does not couple with β-C₁₀H₇OH; Mg and Ca salts. 2-p-Aminophenylglyoxaline, oil turns brown on exposure to the air; di-HCl salt, prisms, darkens about 300°; chlorostannate, needles; picrate, orange, decomposes about 239°; no arsonic acid could be prepared from this compound 2-p-Nitrophenyl-1-methylglyoxaline, pale yellow, m. 116.5° (corrected); HCl salt, elongated plates; chloroaurate, Au-yellow, decomposes 226° (corrected), solubility 1 part in 300 boiling 3 N HCl; nitrate, plates, effervescing 186° (corrected); picrate, m. 212° (corrected). 2-m-Aminophenylglyoxaline, m. 203-4°; the monohydrate partly m. 130-40° and finally 202-3°; di-HCl salt, crystallines with 1 H₂O, m. 282° (decomposition); chlorostannate, prisms; picrate, decomposes 218°. No arsonic acid could be obtained. 2-0-Aminophenylglyoxaline, m. 136-7°; di-HCl salt, m. 234-6°, decomposes slightly higher; chlorostannate, thin plates; NaNO₂ gives a triazine, m. 113-4°, whose HCl salt crystallines in needles; it does not couple with alk. β-C₁₀H₇OH; picrate, m. 211-2°. 4-p-Amino-phenylglyoxaline, m. 98° (corrected); di-HCl salt, darkens 310°; chlorostannate, darkens 310°; dipicrate, yellow, m. 240° (decomposition); the diazo solution gives an intense purple dye with alk. β-C₁₀H₇OH; but a similar color is obtained with NaOH alone. Pauly’s reagent gives an intense red color. Glyoxaline-4(or 5)-phenyl-p-arsonic acid, reddish yellow, does not m. 310°; the yield is very small. 4-o-Aminophenylglyoxaline, m. 131°; di-HCl salt, crystallines with 1 H₂O, which is not lost at 95°, effervesce 256°; NaNO₂ gives a bright yellow solution, from which the triazine seps.; it is insoluble in alkali and does not couple with alk. βC₁₀H₇OH. Dipicrate, decomposes about 200°; normal tartrate, crystallizing with 1.5 H₂O and losing 1 H₂O in vacuum over H₂SO₄, m. 95-7°, effervesces about 130°; α₅₄₆₁ 14.8° (c 0.914 in H₂O); di-d-camphor-10-sulfonate, m. 198-200°, α₅₁₅₁ 21.3° (c 1.0 in H₂O). In the action of 28 cc. Me₂SO₄ on 40 g. 2-phenylglyoxaline, there were obtained 32% unchanged product, 18.2% 2-phenyl-1-methylglyoxaline, pale yellow oil, b₁₅ 175° (HCl salt, with 2 H₂O; chloroaurate, deep yellow, m. 189° (corrected); nitrate, m. about 100°; picrate, m. 133° (corrected); H oxalate, m. 135° (corrected)) and, after evaporation of the aqueous solution with HCl, 26.7% of the methochloride, hygroscopic, m. 272° (chloroaurate, pale yellow, m. 134° (corrected)). Distillation of the methochloride gave 56% of 2-phenyl-1-methylglyoxaline. The therapeutic action of some of these compounds is given.

Journal of the Chemical Society, Abstracts published new progress about 13682-33-2. 13682-33-2 belongs to imidazoles-derivatives, auxiliary class Imidazole,Amine,Benzene, name is 4-(1H-Imidazol-2-yl)aniline, and the molecular formula is C9H9N3, Safety of 4-(1H-Imidazol-2-yl)aniline.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Doebelin, Christelle published the artcileDiscovery and Optimization of a Series of Sulfonamide Inverse Agonists for the Retinoic Acid Receptor-Related Orphan Receptor-a, SDS of cas: 13682-33-2, the publication is Medicinal Chemistry (Sharjah, United Arab Emirates) (2019), 15(6), 676-684, database is CAplus and MEDLINE.

Background: Despite a massive industry endeavor to develop RORalpha-modulators for autoimmune disorders, there has been no indication of efforts to target the close family member RORa for similar indications. This may be due to the misconception that RORa is redundant to RORalpha, or the inherent difficulty in cultivating tractable starting points for RORa. RORa-selective modulators would be useful tools to interrogate the biol. of this understudied orphan nuclear receptor. Objective: The goal of this research effort was to identify and optimize synthetic ligands for RORa starting from the known LXR agonist T0901317. Methods: Fourty-five analogs of the sulfonamide lead (1) were synthesized and evaluated for their ability to suppress the transcriptional activity of RORa, RORalpha, and LXRa in cell-based assays. Analogs were characterized by 1H-NMR, 13C-NMR, and LC-MS anal. The pharmacokinetic profile of the most selective RORa inverse agonist was evaluated in rats with i.p. (i.p.) and per oral (p.o.)dosing. Results: Structure-activity relationship studies led to potent dual RORa/RORalpha inverse agonists as well as RORa-selective inverse agonists (20, 28). LXR activity could be reduced by removing the sulfonamide nitrogen substituent. Attempts to improve the potency of these selective leads by varying substitution patterns throughout the mol. proved challenging.

Medicinal Chemistry (Sharjah, United Arab Emirates) published new progress about 13682-33-2. 13682-33-2 belongs to imidazoles-derivatives, auxiliary class Imidazole,Amine,Benzene, name is 4-(1H-Imidazol-2-yl)aniline, and the molecular formula is C9H9N3, SDS of cas: 13682-33-2.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Donne-Op den Kelder, G. M. published the artcileQSAR studies on mifentidine and related compounds, Synthetic Route of 13682-33-2, the publication is Quantitative Structure-Activity Relationships (1988), 7(2), 60-71, database is CAplus.

The MNDO semiempirical SCF-MO method was used to calculate charge distributions of a series of histamine H₂-receptor antagonists. The investigated compounds concerned mifentidine analogs, RC₆H₄N:CHNHR¹-4, (R = heterocyclics; R¹ = Me, Et, iso-Pr, Pr). A correlation was found between H₂-antagonistic activity as determined by inhibition of specific [³H]-tiotidine binding to the H₂ receptors of a guinea pig cortex preparation, and the net at. charges of 2 of the atoms in the heterocycle. The binding capacity of the ligand mol. to the receptor was enhanced when the electronic population of atom and the pos. charge on the proton were higher. Assuming that the difference between both charges might effectively serve as a valuable substitute for the H bond-forming capacity of the X-H group, the conclusion can be drawn that this property of the heterocycle plays an important role in the interaction process of the ligand with its H₂-receptor. The obtained regression equation(s) suggest that the monocation (formamidine moiety protonated) is the species related to pharmacol. activity.

Quantitative Structure-Activity Relationships published new progress about 13682-33-2. 13682-33-2 belongs to imidazoles-derivatives, auxiliary class Imidazole,Amine,Benzene, name is 4-(1H-Imidazol-2-yl)aniline, and the molecular formula is C9H9N3, Synthetic Route of 13682-33-2.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem