Tag: M.W=150-200

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

Nagaraju, Burri published the artcileSynthesis and biological evaluation of pyrazole linked benzothiazole-β-naphthol derivatives as topoisomerase I inhibitors with DNA binding ability, Synthetic Route of 95-24-9, the publication is Bioorganic & Medicinal Chemistry (2019), 27(5), 708-720, database is CAplus and MEDLINE.

A series of new pyrazole linked benzothiazole-β-naphthol derivatives were designed and synthesized using a simple, efficient and ecofriendly route under catalyst-free conditions in good to excellent yields. These derivatives were evaluated for their cytotoxicity on selected human cancer cell lines. Among those, the derivatives 4j, 4k and 4l exhibited considerable cytotoxicity with IC₅₀ values ranging between 4.63 and 5.54 μM against human cervical cancer cells (HeLa). Structure activity relationship was elucidated by varying different substituents on benzothiazoles and pyrazoles. Further, flow cytometric anal. revealed that these derivatives induced cell cycle arrest in G2/M phase and spectroscopic studies such as UV-visible, fluorescence and CD studies showed that these derivatives exhibited good DNA binding affinity. Addnl., these derivatives can effectively inhibit the topoisomerase I activity. Viscosity studies and mol. docking studies demonstrated that the derivatives bind with the minor groove of the DNA.

Bioorganic & 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, Synthetic Route of 95-24-9.

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

Reddy, Ghanta Mahesh published the artcileIdentification and characterization of potential impurities of tizanidine hydrochloride, Application of 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, the publication is Analytical Chemistry: An Indian Journal (2008), 7(8), 586-590, database is CAplus.

During the anal. of laboratory batches of Tizanidine HCl, six impurities were detected by a simple isocratic reverse-phase high performance liquid chromatog. (HPLC) whose area percentage ranged from 0.10 to 0.30%. A through study has been undertaken to isolate and characterize these impurities, LCMS was performed to identify the mass number of the impurities. The structures of the impurities characterized as: N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazole-4-amine hydrochloride [imp A], N-(5-chloro-2,1,3-benzothiadiazol-4-yl)thiourea (imp B), dimer of Tizanidine HCl (imp C), S-methyl-N-(5-chloro-2,1,3-benzothiadiazol-4-yl)-isothiouronium iodide (imp D), 4-amino-5-chloro-2,1,3-benzothiadiazole (imp E), and N,N-bis(5-chloro-2,1,3-benzothiadiazol-4-yl)-N-(4,5-dihydro-1H-imidazol-2-yl)guanidine (imp F).

Analytical Chemistry: An Indian Journal published new progress about 30536-19-7. 30536-19-7 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, and the molecular formula is C6H4ClN3S, Application of 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine.

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

Mishra, Chandra Bhushan published the artcileDiscovery of Potent Carbonic Anhydrase Inhibitors as Effective Anticonvulsant Agents: Drug Design, Synthesis, and In Vitro and In Vivo Investigations, HPLC of Formula: 95-24-9, the publication is Journal of Medicinal Chemistry (2021), 64(6), 3100-3114, database is CAplus and MEDLINE.

Two sets of benzenesulfonamide-based effective human carbonic anhydrase (hCA) inhibitors have been developed using the tail approach. The inhibitory action of these novel mols. was examined against four isoforms: hCA I, hCA II, hCA VII, and hCA XII. Most of the mols. disclosed low to medium nanomolar range inhibition against all tested isoforms. Some of the synthesized derivatives selectively inhibited the epilepsy-involved isoforms hCA II and hCA VII, showing low nanomolar affinity. The anticonvulsant activity of selected sulfonamides was assessed using the maximal electroshock seizure (MES) and s.c. pentylenetetrazole (s.c.-PTZ) in vivo models of epilepsy. These potent CA inhibitors effectively inhibited seizures in both epilepsy models. The most effective compounds17(I) and 22(II) showed long duration of action and abolished MES-induced seizures up to 6 h after drug administration. These sulfonamides were found to be orally active anticonvulsants, being nontoxic in neuronal cell lines and in animal models.

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, HPLC of Formula: 95-24-9.

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

Korobkov, V. S. published the artcileElectronic spectra of 2,1,3-benzothiadiazole and its derivatives, Recommanded Product: 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, the publication is Spektroskopiya, Metody i Primenenie, Akad. Nauk SSSR, Sibirsk. Otd. (1964), 130-1, database is CAplus.

The ultraviolet absorption spectra, 2110-4400 A., were obtained for 2,1,3-benzothiadiazole, 4,7-dibromo-, 4-amino-5-chloro-, 4-amino-5-bromo-, 4-amino-5,7-dichloro-, 4-amino-5,7-dibromo-, and tetrabromotetrahydro-2,1,3-benzothiazole, 3′,4′-dichlorohydro-1,2-naphth-1,2,3-thiadiazole, and 4′-chloro-1′,2′-naphth-2,1,3-thiadiazole. In general, the typical spectra of condensed aromatic rings were found.

Spektroskopiya, Metody i Primenenie, Akad. Nauk SSSR, Sibirsk. Otd. published new progress about 30536-19-7. 30536-19-7 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, and the molecular formula is C6H4ClN3S, Recommanded Product: 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine.

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

Liu, Hongtao published the artcileIdentification of N-benzothiazolyl-2-benzenesulfonamides as novel ABCA1 expression upregulators, SDS of cas: 95-24-9, the publication is RSC Medicinal Chemistry (2020), 11(3), 411-418, database is CAplus and MEDLINE.

ATP binding cassette transporter A1 (ABCA1) is a critical transporter that mediates cellular cholesterol efflux from macrophages to apolipoprotein A-I (ApoA-I). Therefore, increasing the expression level of ABCA1 is anti-atherogenic and ABCA1 expression upregulators have become novel choices for atherosclerosis treatment. In this study, a series of N-benzothiazolyl-2-benzenesulfonamides, based on the structure of WY06 discovered in our laboratory, were designed and synthesized as novel ABCA1 expression upregulators. Based on an in vitro ABCA1 upregulatory cell model, ABCA1 upregulation of target compounds was evaluated. Compounds 6c, 6d, and 6i have good upregulated ABCA1 expression activities, with EC₅₀ values of 0.97, 0.37, and 0.41μM, resp. A preliminary structure-activity relationship is summarized. Replacing the methoxy group on the benzothiazole moiety of WY06 with a fluorine or chlorine atom and exchanging the ester group with a cyano group resulted in more potent ABCA1 upregulating activity. Moreover, compound 6i increased ABCA1 mRNA and protein expression and significantly promoted cholesterol efflux in RAW264.7 cells. In conclusion, N-benzothiazolyl-2-benzenesulfonamides were identified as novel ABCA1 expression upregulators.

RSC 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, SDS of cas: 95-24-9.

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

Pawde, A. V. published the artcileSynthesis and evaluation of antimicrobial, antioxidant activities of pyrido[3,2-d]pyrazolo[3,2-b]-4H-pyrimido[5,6-e]-4H-pyrimido[2,3-b]benzothiazole derivatives, HPLC of Formula: 95-24-9, the publication is Journal of Applicable Chemistry (Lumami, India) (2019), 8(2), 642-646, database is CAplus.

The objective of the present investigation was to synthesize 3-cyano-4-oxo-2-(methylthio)-6-N-Ph pyrido[3,2-d]pyrazolo[3,2-b]pyrimidine by condensation of 1-phenyl-1H-pyrazolo[3,4-b]pyridine-3-amine with Et cyano bis(methylthio)acrylate which on further condensation with various 2-amino 1/2/3/4-substituted benzothiazoles gives 15-imino-14-oxo-12-N-Ph pyrido[3,2-d]pyrazolo[3,2-b]-4H-pyrimido[5,6-e]-4H-pyrimido[2,3-b]benzothiazole and their 1/3 substituted derivatives I (R¹ = H, CH₃, OCH₃, Cl, NO₂; R² = H, CH₃). These newly synthesized compounds were further screened for antimicrobial and antioxidant properties.

Journal of Applicable Chemistry (Lumami, India) 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, HPLC of Formula: 95-24-9.

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

Pawde, A. V. published the artcileSynthesis and biological evaluation of some newly synthesized thiazolo-pyrimido-pyrimidobenzothiazoles, Synthetic Route of 95-24-9, the publication is European Journal of Biomedical and Pharmaceutical Sciences (2021), 8(4), 256-258, database is CAplus.

Condensation of 2-amino-5-methylthiazole with bis(methylthio)methylene malononitrile give 6-cyano-5-imino-2-methyl-7-(methylthio)-5H-thiazolo[3,2-a]pyrimidine. Which on further condensation with various 2-amino-substituted benzothiazoles yield 12, 13-diimino-9-methyl- thiazolo[2,3-a]-4H-pyrimido[4,5-d]-4H-pyrimido[2,1-b]benzothiazoles I (R¹ = H, Cl; R² = H, Me, OMe, F, Cl, NO₂; R³ = H, Me). Some of the newly synthesized compounds have been screened for their antimicrobial and antioxidant activity.

European Journal of Biomedical and Pharmaceutical Sciences 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, Synthetic Route of 95-24-9.

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

Tsuruoka, Akihiko published the artcileSynthesis and antifungal activity of novel thiazole-containing triazole antifungals. II. Optically active ER-30346 and its derivatives, Recommanded Product: 5-Chlorothiazolo[5,4-b]pyridin-2-amine, the publication is Chemical & Pharmaceutical Bulletin (1998), 46(4), 623-630, database is CAplus and MEDLINE.

A series of novel thiazole-containing triazole antifungals, I (R₁ = Ph, 4-FC₆H₄, Q, etc.) and II (X = CH, N, Y = Cl, F, CSNH₂, etc.), was synthesized and evaluated for antifungal activity against a variety of clin. isolated pathogenic fungi in vitro and against systemic candidosis in vivo. These compounds showed potent antifungal activities in vitro and in vivo. In particular, (2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-2-(2,4-difluorophenyl)-1-(1H-1 ,2,4-triazol-1-yl)-2-butanol (ER-30346) showed potent and well-balanced in vitro activities and potent in vivo efficacy, and had a good safety profile.

Chemical & Pharmaceutical Bulletin published new progress about 31784-71-1. 31784-71-1 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorothiazolo[5,4-b]pyridin-2-amine, and the molecular formula is C9H21NO3, Recommanded Product: 5-Chlorothiazolo[5,4-b]pyridin-2-amine.

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

Altug-Tasa, Burcugul published the artcileDesign, Synthesis and Biological Evaluation of a Novel Series of Thiadiazole- Based Anticancer Agents as Potent Angiogenesis Inhibitors, Category: thiazole, the publication is Anti-Cancer Agents in Medicinal Chemistry (2021), 21(15), 2041-2049, database is CAplus and MEDLINE.

Thiadiazole has attracted a great deal of interest as a versatile heterocycle for the discovery and development of potent anticancer agents. Thiadiazole derivatives exert potent antitumor activity against a variety of human cancer cell lines through various mechanisms. The goal of this work was to design and synthesize thiadiazole-based anticancer agents with anti-angiogenic activity. N-aryl-2-[(5-(aryl)amino-1,3,4-thiadiazol-2-yl)thio]acetamides (4a-r) were synthesized via the reaction of 5-(aryl)amino-1,3,4-thiadiazole-2(3H)-thiones with N-(aryl)-2-chloroacetamides in the presence of potassium carbonate. The compounds were investigated for their cytotoxic effects on three cancer (A549, HepG2, SH-SY5Y), two normal (HUVEC and 3T3-L1) cell lines using MTT and WST-1 assays. In order to examine whether the compounds have anti-angiogenic effects or not, HUVECs were cultured on matrigel matrix to create a vascular-like tube formation. Compounds 4d, 4m and 4n were more effective on A549 human lung adenocarcinoma cells than cisplatin. The IC₅₀ values of compounds 4d, 4m and 4n for A549 cell line were found to be 7.82 ± 0.4, 12.5 ± 0.22, 10.1 ± 0.52 μM, resp. when compared with cisplatin (IC₅₀= 20 ± 0.51 μM), while their IC₅₀ values for HUVEC cell line were determined as 138.7 ± 0.84, 78 ± 0.44, 177.6 ± 0.2 μM, resp. after 48 h of the treatment. The concentrations (10-20-50 μM) of compounds 4d, 4e, 4l, 4m, 4n, 4q and 4r were found to inhibit vascular like tube formation. According to their anticancer and anti-angiogenic effects, compounds 4d, 4m and 4n may be potential anticancer agents for further in vivo studies.

Anti-Cancer Agents in 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, Category: thiazole.

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