Category: 620-20-2

Cardoso, David S. P. published the artcileAlkylated monoterpene indole alkaloid derivatives as potent P-glycoprotein inhibitors in resistant cancer cells, HPLC of Formula: 620-20-2, the publication is European Journal of Medicinal Chemistry (2021), 112985, database is CAplus and MEDLINE.

Aiming at generating a series of monoterpene indole alkaloids with enhanced multidrug resistance (MDR) reversing activity in cancer, two major epimeric alkaloids isolated from Tabernaemontana elegans, tabernaemontanine and dregamine, were derivatized by alkylation of the indole nitrogen. Twenty-six new derivatives were prepared by reaction with different aliphatic and aromatic halides, whose structures were elucidated mainly by NMR, including 2D NMR experiments Their MDR reversal ability was evaluated through a functional assay, using as models resistant human colon adenocarcinoma and human ABCB1-gene transfected L5178Y mouse lymphoma cells, overexpressing P-glycoprotein (P-gp), by flow cytometry. A considerable increase of activity was found for most of the derivatives, being the strongest P-gp inhibitors those sharing N-phenethyl moieties, displaying outstanding inhibitory activity, associated with weak cytotoxicity. Chemosensitivity assays were also performed in a model of combination chemotherapy in the same cell lines, by studying the in vitro interactions between the compounds and the antineoplastic drug doxorubicin. Most of the compounds have shown strong synergistic interactions with doxorubicin, highlighting their potential as MDR reversers. QSAR models were also explored for insights on drug-receptor interaction, and it was found that lipophilicity and bulkiness features were associated with inhibitory activity, although linear correlations were not observed

European Journal of Medicinal Chemistry published new progress about 620-20-2. 620-20-2 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Benzyl chloride,Benzene, name is 3-Chlorobenzylchloride, and the molecular formula is C7H6Cl2, HPLC of Formula: 620-20-2.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Emami, Leila published the artcileNovel N-substituted isatin-ampyrone Schiff bases as a new class of antiproliferative agents: Design, synthesis, molecular modeling and in vitro cytotoxic activity, COA of Formula: C7H6Cl2, the publication is Journal of Heterocyclic Chemistry (2022), 59(7), 1144-1159, database is CAplus.

Thirteen novel isatin-ampyrone Schiff bases derivatives such as I [X = H, Cl; R = H, 3-F, 4-OMe, etc.] were synthesized by the reaction of isatins and benzyl halides followed by condensation with ampyrone. In vitro cytotoxic activity of these new Schiff bases against three human tumor cell lines (MCF-7, A549, and SCOV3) as well as normal breast cell line (MCF-10A) were evaluated by MTT assay. Structure-activity relationship of the tested compounds revealed that chlorine group at C-5 position of the isatin ring significantly increased the cytotoxic activity. This study generally led to introduce a highly active mol. I [X = Cl; R = 3-Cl] with IC₅₀ values of 5.12, 25.5, and 12.9μM, on MCF-7, A549, and SCOV3, resp. Furthermore, mol. docking studies of the synthesized compounds were also done to investigate their binding modes to toward VEGFR-2 and JNK3-MAP kinase as the main targets for isatin-containing anticancer agents. Binding free energy values of the compounds showed pos. correlation with their cytotoxic activities. To confirm the docking results, mol. docking simulations of potent compound I [X = Cl; R = 3-Cl] against VEGFR-2 and JNK3 MAP kinase were also performed. According to the cytotoxic results and in silico ADMET predictions together, I [X = Cl; R = 3-Cl] could be considered as a potent candidate for the future anticancer studies.

Journal of Heterocyclic Chemistry published new progress about 620-20-2. 620-20-2 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Benzyl chloride,Benzene, name is 3-Chlorobenzylchloride, and the molecular formula is C7H6Cl2, COA of Formula: C7H6Cl2.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Xu, Shiyan published the artcileReagent Control Enables Selective and Regiodivergent Opening of Unsymmetrical Phenonium Ions, Synthetic Route of 620-20-2, the publication is Journal of the American Chemical Society (2020), 142(18), 8090-8096, database is CAplus and MEDLINE.

The first examples of selective and regiodivergent chlorination of unsym. benzyl-substituted epoxides, I [R = 4-methoxyphenyl, Ph, 2H-1,3-benzodioxol-5-yl, 1-[(4-methylbenzene)sulfonyl]-2,3-dihydro-1H-indol-5-yl, etc.; R¹ = Pr, 4-methoxyphenyl, 4-cyanobutyl, 4-(benzyloxy)butyl, etc.] have been reported. These reactions are enabled by the dual role of SnCl₄ and TiCl₄ as Lewis acids and chloride nucleophiles. Reagent control dictates addition of chloride at either the substituted internal position (SnCl₄) or unsubstituted terminal position (TiCl₄) of the phenonium ion. These reactions are highly selective, stereospecific, and operationally simple, and proceed in good to excellent yields. Diverse product utility is demonstrated.

Journal of the American Chemical Society published new progress about 620-20-2. 620-20-2 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Benzyl chloride,Benzene, name is 3-Chlorobenzylchloride, and the molecular formula is C7H5Br2F, Synthetic Route of 620-20-2.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Safakish, Mahdieh published the artcileNovel Benzoxazin-3-one Derivatives: Design, Synthesis, Molecular Modeling, Anti-HIV-1 and Integrase Inhibitory Assay, Related Products of chlorides-buliding-blocks, the publication is Medicinal Chemistry (Sharjah, United Arab Emirates) (2020), 16(7), 938-946, database is CAplus and MEDLINE.

Integrase is a validated drug target for anti-HIV-1 therapy. The second generation integrase inhibitors display π-stacking interaction ability with 3′-end nucleotide as a streamlined metal chelating pharmacophore. In this study, we introduced benzoxazin-3-one scaffold for integrase inhibitory potential as bioisostere replacement strategy of 2-benzoxazolinone. Mol. modeling studies revealed that amide functionality alongside oxadiazole heteroatoms and sulfur in the second position of oxadiazole ring could mimic the metal chelating pharmacophore. The halobenzyl ring occupies hydrophobic site created by the cytidylate nucleotide (DC-16). The most potent and selective compound displayed 110μM IC₅₀ with a selectivity index of more than 2.

Medicinal Chemistry (Sharjah, United Arab Emirates) published new progress about 620-20-2. 620-20-2 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Benzyl chloride,Benzene, name is 3-Chlorobenzylchloride, and the molecular formula is C7H6Cl2, Related Products of chlorides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Langston, Steven P. published the artcileDiscovery of TAK-981, a First-in-Class Inhibitor of SUMO-Activating Enzyme for the Treatment of Cancer, Formula: C7H6Cl2, the publication is Journal of Medicinal Chemistry (2021), 64(5), 2501-2520, database is CAplus and MEDLINE.

SUMOylation is a reversible post-translational modification that regulates protein function through covalent attachment of small ubiquitin-like modifier (SUMO) proteins. The process of SUMOylating proteins involves an enzymic cascade, the first step of which entails the activation of a SUMO protein through an ATP-dependent process catalyzed by SUMO-activating enzyme (SAE). Here, we describe the identification of TAK-981, a mechanism-based inhibitor of SAE which forms a SUMO-TAK-981 adduct as the inhibitory species within the enzyme catalytic site. Optimization of selectivity against related enzymes as well as enhancement of mean residence time of the adduct were critical to the identification of compounds with potent cellular pathway inhibition and ultimately a prolonged pharmacodynamic effect and efficacy in preclin. tumor models, culminating in the identification of the clin. mol. TAK-981.

Journal of Medicinal Chemistry published new progress about 620-20-2. 620-20-2 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Benzyl chloride,Benzene, name is 3-Chlorobenzylchloride, and the molecular formula is C7H6Cl2, Formula: C7H6Cl2.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Wang, Jiabao published the artcileNickel-catalyzed reductive benzylation of tertiary alkyl halides with benzyl chlorides and chloroformates, Product Details of C7H6Cl2, the publication is Organic Chemistry Frontiers (2021), 8(12), 2944-2948, database is CAplus.

Ni-Catalyzed reductive cross-coupling of tertiary alkyl halides with benzyl chlorides and chloroformates has been developed, which provides an efficient method for the construction of benzylated all-carbon quaternary centers in moderate to excellent yields with high functional group tolerance.

Organic Chemistry Frontiers published new progress about 620-20-2. 620-20-2 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Benzyl chloride,Benzene, name is 3-Chlorobenzylchloride, and the molecular formula is C7H14N4, Product Details of C7H6Cl2.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Wang, Dungai published the artcileUnsymmetrical Disulfides Synthesis via Cs₂CO₃-Catalyzed Three-Component Reaction in Water, Synthetic Route of 620-20-2, the publication is Advanced Synthesis & Catalysis (2020), 362(22), 4991-4995, database is CAplus.

An unsym. disulfide synthesis by Cs₂CO₃-catalyzed three-component coupling reaction of thioacetates RSC(O)Me (R = 4-CH₃OC₆H₄, CH₂C₆H₅, oxolan-2-ylmethyl, etc.), sodium thiosulfate, and benzyl halide R¹CH₂Cl (R¹ = C₆H₅, 4-BrC₆H₄, 1-naphthyl, etc.) in water has been described. The safe, stable, and non-toxic Na₂S₂O₃ was invoked as the sulfur-source, successfully avoiding the odor generation in the process of S-S bond formation. A wide range of substrate suitability and appropriate functional group tolerance were observed for the transformation. Notably, the approach reported here was compatible with various biomols. including glucose, coumarin, and quinolinone.

Advanced Synthesis & Catalysis published new progress about 620-20-2. 620-20-2 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Benzyl chloride,Benzene, name is 3-Chlorobenzylchloride, and the molecular formula is C12H10F2Si, Synthetic Route of 620-20-2.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Aliabadi, Alireza published the artcileSynthesis and cytotoxicity evaluation of N-(5-(substituted-benzylthio)-1,3,4 thiadiazole-2-yl)-2-p-nitrophenylacetamide derivatives as potential anticancer agents, Recommanded Product: 3-Chlorobenzylchloride, the publication is Iranian Journal of Chemistry & Chemical Engineering (2019), 38(1), 49-55, database is CAplus.

Cancer is a big global problem and is one of the top and main causes of mortality in developed countries. Many of the current treatments and anticancer therapeutics have problems with severe side effects and on the other hand, the drug resistance is also another obstacle in the cancer chemotherapy. Hence, there is a strong demand for the discovery and development of effective new antineoplastic therapies. According to the in vitro effectiveness of 1,3,4-thiadiazole based compounds as anticancer agents, new 1,3,4-thiadiazole based derivatives with various electron withdrawing and electron donating moieties were synthesized and tested by MTT assay against three cancerous cell lines. PC3 (Prostate cancer), U87-C-531 (Glioblastoma) and MDA-MB-231 (Breast cancer) cell lines were applied for MTT assay and obtained results were compared to imatinib. Study of the structure activity relationship of prepared compounds showed electron withdrawing substituents such as Cl, F and NO₂ enhanced the anticancer properties compared to compound without any substituent (compound 3l) or compounds with electron donating (methoxy) substituent (compounds 3j and 3k). Totally, compound 3a (IC₅₀ = 10.6 μM) showed superior activity against PC3 cell line and compounds 3d (IC₅₀ = 10.3 μM), 3h (IC₅₀ = 12.5 μM) and 3j (IC₅₀ = 11.3 μM) exhibited higher activity against MDA-MB-231 cell line compared to imatinib as reference drug.

Iranian Journal of Chemistry & Chemical Engineering published new progress about 620-20-2. 620-20-2 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Benzyl chloride,Benzene, name is 3-Chlorobenzylchloride, and the molecular formula is C7H6Cl2, Recommanded Product: 3-Chlorobenzylchloride.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Tehrani, Maliheh Barazandeh published the artcilePhthalimide-1,2,3-triazole hybrid compounds as tyrosinase inhibitors; synthesis, biological evaluation and molecular docking analysis, Computed Properties of 620-20-2, the publication is Journal of Molecular Structure (2019), 86-93, database is CAplus.

A novel series of phthalimide-1,2,3-triazole hybrids linked to benzyl ring containing different substituents were synthesized and evaluated for their tyrosinase inhibitory activity (inhibitory activity and inhibition kinetic). It was found that compounds 2-((1-(2-nitrobenzyl)-1H-1,2,3-triazol-4-yl)methyl)isoindoline-1,3-dione (I) and 2-((1-(2-bromobenzyl)-1H-1,2,3-triazol-4-yl)methyl)isoindoline-1,3-dione (II), exhibited the best tyrosinase inhibitory activity, with IC₅₀ values of 26.20 ± 1.55 and 26.55 ± 2.31 μM, resp. The inhibition kinetic anal. of I indicated that the compound inhibited tyrosinase in a competitive manner. Moreover, mol. docking anal. was performed to study the interactions and binding modes of the tested compounds Docking results confirmed that the active inhibitors well accumulated in the mushroom tyrosinase active site.

Journal of Molecular Structure published new progress about 620-20-2. 620-20-2 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Benzyl chloride,Benzene, name is 3-Chlorobenzylchloride, and the molecular formula is C10H14O2, Computed Properties of 620-20-2.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Nafie, Mohamed S. published the artcileControl of ER-positive breast cancer by ERα expression inhibition, apoptosis induction, cell cycle arrest using semisynthetic isoeugenol derivatives, Product Details of C7H6Cl2, the publication is Chemico-Biological Interactions (2022), 109753, database is CAplus and MEDLINE.

New semi-synthetic effective and safe anticancer agents isoeugenol derivatives were synthesized, characterized, and screened for their cytotoxic activity against MCF-7. Moreover, their selective cytotoxicity was assessed against MCF-10A. Three derivatives, 2, 8 and 10 were significantly more active than the reference drug 5-FU with IC50 values of 6.59, 8.07 and 9.63 and 30.93 μM, resp. Also interestingly, these derivatives demonstrated some degree of selectivity to cancer cells over normal cells. Furthermore, derivative 2 was subjected to other in vitro experiments against MCF-7 where it inhibited colony formation by 87.5% and lowered ERα concentration to 395.7 pg/mL compared to 1129 pg/mL in untreated control cells. In continuation of the investigation, the apoptotic activity of compound 2, was assessed where it significantly enhanced total apoptotic cell death by 9.16-fold (18.70% compared to 1.64% for the untreated MCF-7 control cells) and arrested the cell cycle at the G2/M phase. Furthermore, the mol. mechanism of apoptotic activity was investigated at both the gene (RT-PCR) and protein (western plotting) levels where upregulation of pro-apoptotic and down regulation of anti-apoptotic genes was detected. Addnl., compound 2 treatment enhanced the antioxidant (GSH, CAT, SOD) activities. Finally, in vivo experiments verified the effective anticancer activity of compound 2 through inhibition of tumor proliferation by 47.6% compared to 22.9% for 5-FU and amelioration of the hematol., biochem., and histopathol. examinations near normal. In effect, compound 2 can be viewed as a promising semi-synthetic derivative of isoeugenol with some degree of selectivity for management of breast cancer through apoptotic induction and ERα downregulation.

Chemico-Biological Interactions published new progress about 620-20-2. 620-20-2 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Benzyl chloride,Benzene, name is 3-Chlorobenzylchloride, and the molecular formula is C7H6Cl2, Product Details of C7H6Cl2.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics