Tag: M.W=200-250

Nath, J. P. published the artcileSynthesis of some 7-substituted 8-hydroxyquinoline derivatives of thiazoles and oxazoles as potential pesticides, Quality Control of 56503-96-9, the publication is Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1981), 20B(7), 606-7, database is CAplus.

Mannich reaction of 8-hydroxyquinoline with PhCHO and I (R = H, Cl, Br; R¹ = Ph, 4-ClC₆H₄, 4-BrC₆H₄, 4-HOC₆H₄, 4-MeO(C₆H₄, 3-O₂NC₆H₄, 4-O₂NC₆H₄, 4-MeC₆H₄, α-,β-naphthyl; X = O, S) gave the title compounds (II). II showed bactericidal and fungicidal activity.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry published new progress about 56503-96-9. 56503-96-9 belongs to thiazole, auxiliary class Thiazole,Amine,Naphthalene, name is 4-(Naphthalen-1-yl)thiazol-2-amine, and the molecular formula is C13H10N2S, Quality Control of 56503-96-9.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Hanke, Thomas published the artcileAminothiazole-Featured Pirinixic Acid Derivatives As Dual 5-Lipoxygenase and Microsomal Prostaglandin E₂ Synthase-1 Inhibitors with Improved Potency and Efficiency in Vivo, Related Products of thiazole, the publication is Journal of Medicinal Chemistry (2013), 56(22), 9031-9044, database is CAplus and MEDLINE.

Dual inhibition of microsomal prostaglandin E₂ synthase-1 (mPGES-1) and 5-lipoxygenase (5-LO) is currently pursued as potential pharmacol. strategy for treatment of inflammation and cancer. Here we present a series of 26 novel 2-aminothiazole-featured pirinixic acid derivatives as dual 5-LO/mPGES-1 inhibitors with improved potency (exemplified by compound 2-[(4-chloro-6-{[4-(naphthalen-2-yl)-1,3-thiazol-2-yl]-amino}-pyrimidin-2-yl)-sulfanyl]-octanoic acid (I) with IC₅₀ = 0.3 and 0.4 μM, resp.) and bioactivity in vivo. Computational anal. presumes binding sites of I at the tip of the 5-LO catalytic domain and within a subpocket of the mPGES-1 active site. Compound I (10 μM) hardly suppressed cyclooxygenase (COX)-1/2 activities, failed to inhibit 12/15-LOs, and is devoid of radical scavenger properties. Finally, compound I reduced vascular permeability and inflammatory cell infiltration in a zymosan-induced mouse peritonitis model accompanied by impaired levels of cysteinyl-leukotrienes and prostaglandin E₂. Together, 2-aminothiazole-featured pirinixic acids represent potent dual 5-LO/mPGES-1 inhibitors with an attractive pharmacol. profile as anti-inflammatory drugs.

Journal of Medicinal Chemistry published new progress about 56503-96-9. 56503-96-9 belongs to thiazole, auxiliary class Thiazole,Amine,Naphthalene, name is 4-(Naphthalen-1-yl)thiazol-2-amine, and the molecular formula is C13H10N2S, Related Products of thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Oegretir, Cemil published the artcileDetermination and Evaluation of Acid Dissociation Constants of Some Substituted 2-Aminobenzothiazole Derivatives, Safety of 4-(Naphthalen-1-yl)thiazol-2-amine, the publication is Journal of Chemical & Engineering Data (2008), 53(2), 422-426, database is CAplus.

The acid dissociation constants of some 4- and/or 6-substituted 2-aminobenzothiazole and 4-substituted thiazole derivatives were determined spectroscopically. With the exception of a few, the first protonation was found to occur on the amino group. In some mols. where prototropic tautomerism is possible, a change-over in the protonation mechanism was observed The first protonation under these circumstances was found to occur on the imino nitrogen atom. The second protonation takes place on the thiazole ring nitrogen atom.

Journal of Chemical & Engineering Data published new progress about 56503-96-9. 56503-96-9 belongs to thiazole, auxiliary class Thiazole,Amine,Naphthalene, name is 4-(Naphthalen-1-yl)thiazol-2-amine, and the molecular formula is C13H10N2S, Safety of 4-(Naphthalen-1-yl)thiazol-2-amine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Liu, Jingbao published the artcileDesign, synthesis, and biological evaluation of 2-substituted ethenesulfonic acid ester derivatives as selective PTP1B inhibitors, Name: 4-(Naphthalen-1-yl)thiazol-2-amine, the publication is Pharmazie (2015), 70(7), 446-451, database is CAplus and MEDLINE.

Fifteen 2-substituted ethenesulfonic acid ester derivatives were designed, synthesized, and evaluated for the inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) and T-Cell protein tyrosine phosphatase (TCPTP). The structural activity relationship (SAR) of these compounds were discussed to clarify the impact of the linker and the optimized tail on the inhibitory activity of PTP1B and selectivity over TCPTP. Most of the compounds exhibited excellent inhibitory activities against PTP1B with IC₅₀ values of 1.5-8.9 μM. SAR anal. revealed that the substituents at the hydrophobic tail significantly alter the inhibitory activity against PTP1B and selectivity over TCPTP, e.g. compound Ethyl-2-(4-(3-(4-(2-chlorophenyl)thiazol-2-ylamino)propoxy)phenyl)ethenesulfonate showed excellent inhibitory activity to PTP1B with IC₅₀ = 7.8 μM, and ∼6-fold selectivity over TCPTP. Combined with our previous findings, that the linker length and the substituted hydrophobic tail had decisive influence on the PTP1B inhibitory activity and selectivity was confirmed.

Pharmazie published new progress about 56503-96-9. 56503-96-9 belongs to thiazole, auxiliary class Thiazole,Amine,Naphthalene, name is 4-(Naphthalen-1-yl)thiazol-2-amine, and the molecular formula is C13H10N2S, Name: 4-(Naphthalen-1-yl)thiazol-2-amine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Song, Jung Min published the artcileA tetra(ethylene glycol) derivative of benzothiazole aniline ameliorates dendritic spine density and cognitive function in a mouse model of Alzheimer’s disease, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Experimental Neurology (2014), 105-113, database is CAplus and MEDLINE.

We recently reported that the tetra(ethylene glycol) derivative of benzothiazole aniline, BTA-EG₄, acts as an amyloid-binding small mol. that promotes dendritic spine d. and cognitive function in wild-type mice. This raised the possibility that BTA-EG₄ may benefit the functional decline seen in Alzheimer’s disease (AD). In the present study, we directly tested whether BTA-EG₄ improves dendritic spine d. and cognitive function in a well-established mouse model of AD carrying mutations in APP, PS1 and tau (APP_swe;PS1_M146V;tau_P301L, 3xTg AD mice). We found that daily injections of BTA-EG₄ for 2 wk improved dendritic spine d. and cognitive function of 3xTg AD mice in an age-dependent manner. Specifically, BTA-EG₄ promoted both dendritic spine d. and morphol. alterations in cortical layers II/III and in the hippocampus at 6-10 mo of age compared to vehicle-injected mice. However, at 13-16 mo of age, only cortical spine d. was improved without changes in spine morphol. The changes in dendritic spine d. correlated with Ras activity, such that 6-10 mo old BTA-EG₄ injected 3xTg AD mice had increased Ras activity in the cortex and hippocampus, while 13-16 mo old mice only trended toward an increase in Ras activity in the cortex. Finally, BTA-EG₄ injected 3xTg AD mice at 6-10 mo of age showed improved learning and memory; however, only minimal improvement was observed at 13-16 mo of age. This behavioral improvement corresponds to a decrease in soluble Aβ 40 levels. Taken together, these findings suggest that BTA-EG₄ may be beneficial in ameliorating the synaptic loss seen in early AD.

Experimental Neurology published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C4H10Br2CoO2, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Etse, Koffi Senam published the artcileDevelopment of Thiochroman Dioxide Analogues of Benzothiadiazine Dioxides as New Positive Allosteric Modulators of α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA) Receptors, Quality Control of 1204572-55-3, the publication is ACS Chemical Neuroscience (2021), 12(14), 2679-2692, database is CAplus and MEDLINE.

On the basis of the activity of 1,2,4-benzothiadiazine 1,1-dioxides as pos. allosteric modulators of AMPA receptors, thiochroman 1,1-dioxides were designed applying the isosteric replacement concept. The new compounds expressed strong modulatory activity on AMPA receptors in vitro, although lower than their corresponding benzothiadiazine analogs. The pharmacokinetic profile of three thiochroman 1,1-dioxides (12a, 12b, 12e) was examined in vivo after oral administration, showing that these compounds freely cross the blood-brain barrier. Structural anal. was achieved using X-ray crystallog. after cocrystn. of the racemic compound 12b in complex with the ligand-binding domain of GluA2 (L504Y/N775S). Interestingly, both enantiomers of 12b were found to interact with the GluA2 dimer interface, almost identically to its benzothiadiazine analog, BPAM344 (4). The interactions of the two enantiomers ((R)-12b (I) and (S)-12b (II)) in the cocrystal were further analyzed (mapping Hirshfeld surfaces and 2D fingerprint) and compared to those of 4. Taken together, these data explain the lower affinity on AMPA receptors of thiochroman 1,1-dioxides compared to their corresponding 1,2,4-benzothiadiazine 1,1-dioxides.

ACS Chemical Neuroscience published new progress about 1204572-55-3. 1204572-55-3 belongs to thiazole, auxiliary class Neuronal Signaling,GluR, name is 4-Cyclopropyl-7-fluoro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide, and the molecular formula is C10H11FN2O2S, Quality Control of 1204572-55-3.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Li, Yang published the artcileNear-Infrared Activated Black Phosphorus as a Nontoxic Photo-Oxidant for Alzheimer’s Amyloid-β Peptide, COA of Formula: C14H12N2S, the publication is Small (2019), 15(24), n/a, database is CAplus and MEDLINE.

The inhibition of amyloid-β (Aβ) aggregation by photo-oxygenation has become an effective way of treating Alzheimer’s disease (AD). New near-IR (NIR) activated treatment agents, which not only possess high photo-oxygenation efficiency, but also show low biotoxicity, are urgently needed. Herein, for the first time, it is demonstrated that NIR activated black phosphorus (BP) could serve as an effective nontoxic photo-oxidant for amyloid-β peptide in vitro and in vivo. The nanoplatform BP@BTA (BTA: one of thioflavin-T derivatives) possesses high affinity to the Aβ peptide due to specific amyloid selectivity of BTA. Importantly, under NIR light, BP@BTA can significantly generate a high quantum yield of singlet oxygen (¹O₂) to oxygenate Aβ, thereby resulting in inhibiting the aggregation and attenuating Aβ-induced cytotoxicity. In addition, BP could finally degrade into nontoxic phosphate, which guarantees the biosafety. Using transgenic Caenorhabditis elegans CL2006 as AD model, the results demonstrate that the ¹O₂-generation system could dramatically promote life-span extension of CL2006 strain by decreasing the neurotoxicity of Aβ.

Small published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, COA of Formula: C14H12N2S.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Shukla, Nikunj M. published the artcileStructure-activity relationship studies in substituted sulfamoyl benzamidothiazoles that prolong NF-κB activation, Related Products of thiazole, the publication is Bioorganic & Medicinal Chemistry (2021), 116242, database is CAplus and MEDLINE.

In the face of emerging infectious diseases, there remains an unmet need for vaccine development where adjuvants that enhance immune responses to pathogenic antigens are highly desired. Using high-throughput screens with a cell-based nuclear factor κB (NF-κB) reporter assay, we identified a sulfamoyl benzamidothiazole bearing compound 1 that demonstrated a sustained activation of NF-κB after a primary stimulus with a Toll-like receptor (TLR)-4 agonist, lipopolysaccharide (LPS). Here, we explore systematic structure-activity relationship (SAR) studies on compound 1 that indicated the sites on the scaffold that tolerated modification and yielded more potent compounds compared to 1. The selected analogs enhanced release of immunostimulatory cytokines in the human monocytic cell line THP-1 cells and murine primary dendritic cells. In murine vaccination studies, select compounds were used as co-adjuvants in combination with the Food and Drug Administration approved TLR-4 agonistic adjuvant, monophosphoryl lipid A (MPLA) that showed significant enhancement in antigen-specific antibody titers compared to MPLA alone. Addnl., our SAR studies led to identification of a photoaffinity probe which will aid the target identification and mechanism of action studies in the future.

Bioorganic & Medicinal Chemistry published new progress about 56503-96-9. 56503-96-9 belongs to thiazole, auxiliary class Thiazole,Amine,Naphthalene, name is 4-(Naphthalen-1-yl)thiazol-2-amine, and the molecular formula is C6H12O2, Related Products of thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Kennedy, G. L. Jr. published the artcileInhalation toxicity of dehydrothio-p-toluidine, Category: thiazole, the publication is Food and Chemical Toxicology (1984), 22(4), 289-92, database is CAplus and MEDLINE.

The acute inhalation toxicity of dehydrothio-p-toluidine (DHPT)(I) [92-36-4] was determined by exposing groups of young adult rats for single 4-h periods. Death resulted when the DHPT concentration reached 3.00 mg/L. The subchronic effects of DHPT were studied by exposing male rats to 0.6 mg/L for 10 6-h periods (5 exposure days, 2 rest days, 5 exposure days). Body-weight loss during the exposures was followed by normal weight gain during a 14-day recovery period. Salivation, lacrymation, pawing and chewing motions, rapid respiration, and red nasal discharge occurred during exposure and continued into the recovery period, although they generally abated as the recovery period progressed. Clin. laboratory measurements on blood from exposed rats suggested a hemolytic anemia with injury to the liver and kidneys. Liver changes were characterized by hepatocyte hypertrophy and proliferation of bile-duct epithelial cells. A mild degree of renal tubular degeneration was seen and the spleen showed congestion of red pulp with excessive amounts of hemosiderin. These effects persisted throughout the 2-wk recovery period.

Food and Chemical Toxicology published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, Category: thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Hu, Wan-Ping published the artcileSynthesis, and biological evaluation of 2-(4-aminophenyl)benzothiazole derivatives as photosensitizing agents, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Bioorganic & Medicinal Chemistry (2010), 18(16), 6197-6207, database is CAplus and MEDLINE.

Photodynamic therapy (PDT) employing exogenous photosensitizers is currently being approved for treatment of basal cell carcinoma (BCC). 2-(4-Aminophenyl)benzothiazoles (6) consist of chromophoric structure and absorb light in the UVA (315-400 nm). These results encouraged us to design and synthesize a diversity of 2-phenylbenzothiazoles (6). Studies on the apoptotic mechanism involved in photosensitive effects induced by UVA-activated 6 in BCC cells are carried out in the present article. 6-UVA-treated cells displayed several features of apoptosis, including an increase in the sub-G1 population, a significantly increased annexin V binding, and activation of caspase-3. 6-UVA induced a decrease in mitochondrial membrane potential (Δψ _mt) and ATP via enhanced ROS generation and promoted phosphorylation of extracellular signal-regulated kinase (ERK) and p38 MAPK expression. These results suggest that 6-UVA elicits photosensitive effects in mitochondria processes which involve ERK and p38 activation, and ultimately lead to BCC cell apoptosis.

Bioorganic & Medicinal Chemistry published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica