Day: November 25, 2022

Yan, Bingsong published the artcileColorimetric detection of acetylcholinesterase and its inhibitor based on thiol-regulated oxidase-like activity of 2D palladium square nanoplates on reduced graphene oxide, Product Details of C18H24N6O6S4, the publication is Microchimica Acta (2021), 188(5), 162, database is CAplus and MEDLINE.

A convenient and sensitive colorimetric assay for acetylcholinesterase (AChE) and its inhibitor has been designed based on the oxidase-like activity of {100}-faceted Pd square nanoplates which are grown in situ on reduced graphene oxide (PdSP@rGO). PdSP@rGO can effectively catalyze the oxidation of colorless 3,3′,5,5′-tetramethylbenzidine (TMB) without the assistance of H₂O₂ to generate blue oxidized TMB (oxTMB) with a characteristic absorption peak at 652 nm. In the presence of AChE, acetylthiocholine (ATCh), a typical AChE substrate, is hydrolyzed to thiocholine (TCh). The generated TCh can effectively inhibit the PdSP@rGO-triggered chromogenic reaction of TMB via cheating with Pd, resulting in color fading and decrease in absorbance. Thus, a sensitive probe for AChE activity is constructed with a working range of 0.25-5 mU mL-1 and a limit of detection (LOD) of 0.0625 mU mL-1. Furthermore, because of the inhibition effect of tacrine on AChE, tacrine is also detected through the colorimetric AChE assay system within the concentrations range 0.025-0.4μM with a LOD of 0.00229μM. Hence, a rapid and facile colorimetric procedure to sensitively detect AChE and its inhibitor can be anticipated through modulating the oxidase-like activity of PdSP@rGO.

Microchimica Acta published new progress about 30931-67-0. 30931-67-0 belongs to thiazole, auxiliary class Salt,Hydrazine,Amine,Benzothiazole, name is Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate), and the molecular formula is C11H10O, Product Details of C18H24N6O6S4.

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

Wang, Xin published the artcileA Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions, Formula: C14H18BNO2S, the publication is Organic Letters (2019), 21(20), 8158-8163, database is CAplus and MEDLINE.

Herein, we present an air-stable dianthracenyl monophosphine ligand (diAnthPhos) which can be prepared in two steps from com. available anthracene derivatives The ligand exhibits excellent efficiency for palladium-catalyzed coupling reactions. In particular, Miyaura borylation of heterocycle-containing electrophiles can be facilitated employing the diAnthPhos ligand with a broad substrate scope and low catalyst loading. The valuable synthetic utility of the new ligand is further demonstrated by a one-pot Miyaura borylation/Suzuki coupling protocol for heteroaryl-containing substrates.

Organic Letters published new progress about 791614-90-9. 791614-90-9 belongs to thiazole, auxiliary class Boronate Esters,Boronic acid and ester,Boronic acid and ester, name is 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole, and the molecular formula is C16H10O5, Formula: C14H18BNO2S.

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

Karlsson, H. Jonas published the artcileSynthesis and DNA binding studies of a new asymmetric cyanine dye binding in the minor groove of [poly(dA-dT)]₂, Category: thiazole, the publication is Bioorganic & Medicinal Chemistry (2003), 11(6), 1035-1040, database is CAplus and MEDLINE.

A new asym. cyanine dye has been synthesized and its interaction with different DNA has been investigated. In this dye, BEBO, the structure of the known intercalating cyanine dye BO has been extended with a benzothiazole substituent. The resulting crescent-shape of the mol. is similar to that of the well-known minor groove binder Hoechst 33258. Indeed, comparative studies of BO illustrate a considerable change in binding mode induced by this structural modification. Linear and CD studies indicate that BEBO binds in the minor groove to [poly (dA-dT)]₂, but that the binding to calf thymus DNA is heterogeneous, although still with a significant contribution of minor groove binding. Similar to other DNA binding asym. cyanine dyes, BEBO has a large increase in fluorescence intensity upon binding and a relatively large quantum yield when bound. The minor groove binding of BEBO to [poly (dA-dT)]₂ affords roughly a 180-fold increase in intensity, which is larger than to that of the commonly used minor groove binding probes DAPI and Hoechst 33258.

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, Category: thiazole.

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

Diao, Peng-Cheng published the artcileDiscovery of novel pyrimidine-based benzothiazole derivatives as potent cyclin-dependent kinase 2 inhibitors with anticancer activity, Safety of 6-Chlorobenzothiazol-2-ylamine, the publication is European Journal of Medicinal Chemistry (2019), 196-207, database is CAplus and MEDLINE.

To develop novel CDK2 inhibitors as anticancer agents, a series of novel pyrimidine-based benzothiazole derivatives I (R = 4-(S(O)₂NH₂), 4-(piperidin-1-yl), 3-F, etc.) and II (R¹ = H, F, Cl, Me, MeO; R² = H, Me, F; R³ = Me, NH₂) was designed and synthesized. Initial biol. evaluation demonstrated that some of target compounds displayed potent antitumor activity in vitro against five cancer cell lines. Especially, the analog II (R¹ = F; R² = H; R³ = NH₂) exhibited approx. potency with AZD5438 toward four cells including HeLa, HCT116, PC-3, and MDA-MB-231 with IC₅₀ values of 0.45, 0.70, 0.92, 1.80 μM, resp. More interestingly, the most highly active compound II (R¹ = F; R² = H; R³ = NH₂) in this study also possessed promising CDK2/cyclin A2 inhibitory activities with IC₅₀ values of 15.4 nM, which was almost 3-fold potent than pos. control AZD5438, and mol. docking studies revealed that the analog bound efficiently with the CDK2 binding site. Further studies indicated that compound II (R¹ = F; R² = H; R³ = NH₂) could induce cell cycle arrest and apoptosis in a concentration-dependent manner. These observations suggest that pyrimidine-benzothiazole hybrids represent a new class of CDK2 inhibitors and well worth further investigation aiming to generate potential anticancer agents.

European Journal of Medicinal Chemistry published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C7H5ClN2S, Safety of 6-Chlorobenzothiazol-2-ylamine.

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

Li, M. published the artcileSynthesis and cellular activity of stereochemically-pure 2′-O-(2-methoxyethyl)-phosphorothioate oligonucleotides, Category: thiazole, the publication is Chemical Communications (Cambridge, United Kingdom) (2017), 53(3), 541-544, database is CAplus and MEDLINE.

Stereochem.-pure 2′-O-(2-methoxyethyl)-phosphorothioate (PS-MOE) oligonucleotides were synthesized from new chiral oxazaphospholidine-containing nucleosides. Thermal stability studies showed that the incorporation of Rp-PS linkages increased RNA-binding affinity. In cells, a full Rp-PS-MOE splice-switching oligonucleotide targeting part of the ferrochelatase gene was more potent than its Sp-PS counterpart, but of similar potency to the stereo-random PS-parent sequence.

Chemical Communications (Cambridge, United Kingdom) published new progress about 1192027-04-5. 1192027-04-5 belongs to thiazole, auxiliary class Other Aliphatic Heterocyclic,Amine, name is N,N-Dimethyl-N’-(3-thioxo-3H-1,2,4-dithiazol-5-yl)formimidamide, and the molecular formula is C5H7N3S3, Category: thiazole.

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

Abdelhameed, Ahmed published the artcileSynthesis and antileishmanial evaluation of thiazole orange analogs, Related Products of thiazole, the publication is Bioorganic & Medicinal Chemistry Letters (2020), 30(1), 126725, database is CAplus and MEDLINE.

A series of 23 analogs of thiazole orange derivatives I [R = H, 5-Me, 8-Ph, etc.; R¹ = Me, Et, n-Pr, Bn; X^– = I, CF₃SO₃], II, III and IV, a com. cyanine dye with antileishmanial activity, were synthesized in an effort to increase the selectivity of such compounds while maintaining efficacy. Cyanines possessing substitutions on the quinolinium ring system displayed potency against Leishmania donovani axenic amastigotes that differed little from the parent compound (IC₅₀ 12-42 nM), while ring disjunction analogs were both less potent and less toxic. Changes in DNA melting temperature were modest when synthetic oligonucleotides were incubated with selected analogs (ΔTm ≤ 5°), with ring disjunction analogs showing the least effected on this parameter. Despite the high antileishmanial potency of the target compounds I, II, III and IV, their toxicity and relatively flat SAR suggested that further information regarding the target(s) of these mols. was needed to aid their development as antileishmanials.

Bioorganic & Medicinal Chemistry Letters published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, Related Products of thiazole.

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

Zhang, Yan published the artcileSynthesis and insecticidal evaluation of novel sulfide-containing amide derivatives as potential ryanodine receptor modulators, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine, the publication is Chinese Chemical Letters (2022), 33(1), 501-507, database is CAplus.

With the aim of discovering new bioactive pesticides for crop protection, a series of novel sulfide-containing amide derivatives A were efficiently synthesized via a strategy of modifying the “amide” structure of anthranilic diamide insecticides. The single-crystal structures of A2-3 and A4-5 were firstly reported. The bioassay results showed that most of the synthesized compounds display moderate to high insecticidal activities. Particularly, some sulfone-containing compounds, e.g.,A2-3,A3-3 and A6-3, not only possessed favorable lethality rate (50%-100%) against P. xylostella at a concentration of 0.1 mg/L, but also held good activities towards a variety of agricultural pests such as M. separata, C. pipiens pallen, H. armigera and O. nubilalis; the larvicidal activities of A4-1 and A6-1 towards P. xylostella were close to that of chlorantraniliprole at 0.01 mg/L. The calcium imaging experiments revealed that the representative compounds A2-3 and A6-3 are potential ryanodine receptor (RyR) modulators. The structure-activity relationships were discussed in detail. These results provide useful information for further design and development of novel insecticides.

Chinese Chemical Letters published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C5H5ClIN, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine.

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

Shang, Junfeng published the artcileSynthesis and evaluation of novel 1-(((6-substituted benzo[d]thiazol-2-yl)amino)(heteroaryl)methyl)naphthalen-2-ol as pesticidal agents, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine, the publication is Journal of Enzyme Inhibition and Medicinal Chemistry (2022), 37(1), 641-651, database is CAplus and MEDLINE.

To discover new agrochems. with prominent pesticidal properties, a series of novel β-naphthol derivatives containing benzothiazolylamino and various heteroaryl groups I (R = H, CF₃, Cl; Het = pyrazol-5-yl, imidazol-2-yl, pyrimidin-5-yl, etc.) were efficiently synthesized via Betti reaction. The bioassay results showed that most of the synthesized compounds exhibited favorable insecticidal potentials, particularly towards oriental armyworm (50-100% at 200 mg·L^-1) and diamondback moth (50-95% at 10 mg·L^-1). Some compounds possessed LC₅₀ values of 0.0988-5.8864 mg·L^-1 against diamondback moth. Compounds I (R = H; Het = 2-phenyl-2H-1,2,3-triazol-4-yl), I (R = H; Het = 6-chloroimidazo[1,2-a]pyridin-3-yl), I (R = H; Het = 6-bromoimidazo[1,2-a]pyridin-3-yl) also displayed lethality rates of 30-90% against spider mite at the concentration of 100 mg·L^-1. Overall, some compounds could be considered as new insecticidal/acaricidal leading structures for further investigation. The calcium imaging experiments revealed that compound I (R = H; Het = 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl), I (R = H; Het = 2-phenyl-2H-1,2,3-triazol-4-yl), and 1-((benzo[d]thiazol-2-ylamino)(4-methoxyphenyl)- Methyl)naphthalen-2-ol could activate the release of calcium ions in insect (M. separata) central neurons at a higher concentration (50 mg·L^-1). The SAR anal. provided valuable information for further structural modifications.

Journal of Enzyme Inhibition and Medicinal Chemistry published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C12H14O2, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine.

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

Hou, Yue published the artcileA dihedral-angle-controlled mechanochromic luminescent material: Application for pressure sensing, Name: 6-Chlorobenzothiazol-2-ylamine, the publication is Dyes and Pigments (2020), 108505, database is CAplus.

For most of the mechanochromic luminescent (MCL) materials, their mechanisms are based on the phase transition. When they are fabricated into devices or films, the MCL cannot be fully activated due to uncontrollable phase state of the materials. In this study, a new MCL material, (E)-6-chloro-N-(4-(dimethylamino)benzylidene)benzo[d]thiazol-2-amine (CDBTA), functioning based on dihedral-angle change, was reported. The initial state of CDBTA glows green emission (520 nm), while grinding changes its color into yellow-orange (551 nm). The switching between two emission states can be stably switched with high fatigue resistance. The underlying MCL mechanism was verified by crystal analyses on two forms of single crystal, namely Green-form (G-form) and Yellow-form (Y-form), resp. Mols. in G-form crystal adopt the twisted conformation by the rotation of the donor-acceptor (D-A) biplane. The dihedral angle is thus fixed by a variety of intermol. interactions. Under mech. stimuli, these interactions are destructed and the intramol. torsional stress is released. Thus the mols. cannot maintain twisted conformation but form D-A coplane similar to the Y-form. Such dihedral-angle-controlled structural relaxation makes the π-electron highly delocalized to facilitate bathochromic-shift. The MCL stems from the changes of dihedral angle of the D-A biplane rather than that in packing mode or phase state, therefore CDBTA offers the possibility to fully activate the MCL performances when instrumented. Encouraged by this advantage, a CDBTA film sensor for pressure detection was fabricated, which exhibits a gradual red-shift with pressure and low detection limit down to 15.21 MPa.

Dyes and Pigments published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C7H5ClN2S, Name: 6-Chlorobenzothiazol-2-ylamine.

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

Yue, Xiaoping published the artcileBiocatalytic dynamic reductive kinetic resolution of aryl α-chloro β-keto esters: divergent, stereocontrolled synthesis of diltiazem, clentiazem, and siratiazem, Formula: C7H5ClN2S, the publication is Chemical Communications (Cambridge, United Kingdom) (2022), 58(64), 9010-9013, database is CAplus and MEDLINE.

The first systematic study of ketoreductase (KRED)-catalyzed dynamic reductive kinetic resolution (DYRKR) on aryl α-chloro β-keto esters was performed and 15 structurally diverse chiral anti-aryl α-chloro β-hydroxy esters were synthesized in 74-98% isolated yields, along with moderate-to-excellent diastereoselectivity (up to >99 : 1 dr) and good-to-excellent enantioselectivity (mostly >99% ee). LfSDR1-catalyzed complete reduction of 100 g L^-1 of substrate 6b at a ten-gram scale was achieved with a continuous fed-batch strategy, afforded anti-(2S,3S)-1b, the key intermediate of diltiazem, in a record-breaking space-time yield of 96 g L^-1 d^-1. An eight-step synthesis of diltiazem, clentiazem and siratiazem was accomplished in 32-45% overall yields, featuring this versatile biocatalytic reduction reaction as well as an efficient, green chlorination reaction in flow.

Chemical Communications (Cambridge, United Kingdom) published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C12H10F2Si, Formula: C7H5ClN2S.

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