Tag: M.W=200-250

Raza, Hussain published the artcileSynthesis, molecular docking, dynamic simulations, kinetic mechanism, cytotoxicity evaluation of N-(substituted-phenyl)-4-{(4-[(E)-3-phenyl-2-propenyl]-1-piperazinyl} butanamides as tyrosinase and melanin inhibitors: In vitro, in vivo and in silico approaches, Recommanded Product: (E)-1-Cinnamylpiperazine, the publication is Bioorganic Chemistry (2020), 103445, database is CAplus and MEDLINE.

In the current research work, different N-(substituted-phenyl)-4-{(4-[(E)-3-phenyl-2-propenyl]-1-piperazinyl}butanamides have been synthesized according to the protocol described in scheme 1. The synthesis was initiated by reacting various substituted anilines (1a-e) with 4-chlorobutanoyl chloride (2) in aqueous basic medium to give various electrophiles, 4-chloro-N-(substituted-phenyl)butanamides (3a-e). These electrophiles were then coupled with 1-[(E)-3-phenyl-2-propenyl]piperazine (4) in polar aprotic medium to attain the targeted N-(substituted-phenyl)-4-{(4-[(E)-3-phenyl-2-propenyl]-1-piperazinyl}butanamides (5a-e). The structures of all derivatives were identified and characterized by proton-NMR (¹H NMR), carbon-NMR (¹³C NMR) and Infra-Red (IR) spectral data along with CHN anal. The in vitro inhibitory potential of these butanamides was evaluated against Mushroom tyrosinase, whereby all compounds were found to be biol. active. Among them, 5b exhibited highest inhibitory potential with IC₅₀ value of 0.013 ± 0.001μM. The same compound 5b was also assayed through in vivo approach, and it was explored that it significantly reduced the pigments in zebrafish. The in silico studies were also in agreement with aforesaid results. Moreover, these mols. were profiled for their cytotoxicity through hemolytic activity, and it was found that except 5e, all other compounds showed minimal toxicity. The compound 5a also exhibited comparable results. Hence, some of these compounds might be worthy candidates for the formulation and development of depigmentation drugs with min. side effects.

Bioorganic Chemistry published new progress about 87179-40-6. 87179-40-6 belongs to piperazines, auxiliary class Benzenes, name is (E)-1-Cinnamylpiperazine, and the molecular formula is C13H18N2, Recommanded Product: (E)-1-Cinnamylpiperazine.

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

Srivastava, Sanjay K. published the artcileSynthesis of 13-amino costunolide derivatives as anticancer agents, SDS of cas: 87179-40-6, the publication is Bioorganic & Medicinal Chemistry Letters (2006), 16(16), 4195-4199, database is CAplus and MEDLINE.

A number of amino derivatives of costunolide have been synthesized and evaluated for their in vitro cytotoxicity against eight tumor and a non-tumor cell lines. For example, costunolide amino derivative I (R = 3-methylpiperidin-1-yl) showed around 2-fold better cytotoxicity against SW-620 (colon) cell line with improved safety index than costunolide (II). While I (R = 4-hydroxypiperidin-1-yl, 3-hydroxypyrrolidin-1-yl, dimethylamino) have shown around 2- to 3-fold better cytotoxicity against MIAPaCa2 (pancreas), K-562 (leukemia) and PA-1 (ovary) cell lines as well as better safety index in comparison to II. I (R = dimethylamino) also exhibited cytotoxicity against HBL100 (breast) cell line with 2-fold better safety index. Structure-activity relationship has been described.

Bioorganic & Medicinal Chemistry Letters published new progress about 87179-40-6. 87179-40-6 belongs to piperazines, auxiliary class Benzenes, name is (E)-1-Cinnamylpiperazine, and the molecular formula is C7H8BClO2, SDS of cas: 87179-40-6.

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

Jallapally, Anvesh published the artcile2-Butyl-4-chloroimidazole based substituted piperazine-thiosemicarbazone hybrids as potent inhibitors of Mycobacterium tuberculosis, Product Details of C13H18N2, the publication is Bioorganic & Medicinal Chemistry Letters (2014), 24(23), 5520-5524, database is CAplus and MEDLINE.

A series of 2-butyl-4-chloroimidazole based substituted piperazine-thiosemicarbazone hybrids was designed by combining three different pharmacophoric fragments in single mol. architecture. 2-Butyl-4-chloro-1-((3-(4-substituted)piperazin-1-yl)propyl)-1H-imidazole-5-carbaldehydes were prepared by reacting carboxaldehydes with N-alkylpiperazines and were subsequently condensed with thiosemicarbazide to give the desired compounds in very good yields. Among all sixteen compounds screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB), two compounds (E)-2-((2-butyl-4-chloro-1-(3-(4-(o-tolyl)piperazin-1-yl)propyl)-1H-imidazol-5-yl)methylene)hydrazinecarbothioamide and (E)-2-((2-butyl-4-chloro-1-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)-1H-imidazol-5-yl)methylene)hydrazinecarbothioamide were found to be the most potent antitubercular agents (MIC: 3.13 μg/mL) with low toxicity profile.

Bioorganic & Medicinal Chemistry Letters published new progress about 87179-40-6. 87179-40-6 belongs to piperazines, auxiliary class Benzenes, name is (E)-1-Cinnamylpiperazine, and the molecular formula is C13H18N2, Product Details of C13H18N2.

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

Pawara, Rahul published the artcileDesign and synthesis of the novel, selective WZ4002 analogue as EGFR-L858R/T790M tyrosine kinase inhibitors for targeted drug therapy in non-small-cell lung cancer (NSCLC), SDS of cas: 67914-60-7, the publication is Journal of Molecular Structure (2022), 132313, database is CAplus.

To conquer the drug-resistance of first-generation EGFR (epidermal growth factor receptor) kinase inhibitors and second-generation inhibitors’ non-selective toxicities in Non-Small Cell Lung Cancer (NSCLC) patients, a series of WZ4002 derivatives I [R¹ = 4-fluorophenyl, 3,4-dichlorophenyl, 4-bromophenyl, etc.; R² = 3-CH₂=CHC(O)NHC₆H₄, 4-MeC(O)-N(CH₂)₂N-C₆H₄, 3-ClCH₂C(O)NHC₆H₄, etc.] were discovered as novel double mutant EGFR-L858R/T790M TK inhibitors. This objective was attained by employing structure-based drug design and traditional optimization strategies based on the WZ4002 scaffold. Among the synthesized compounds I, representative compounds I [R¹ = 4-chloro-3-fluorophenyl, 4-bromophenyl; R² = 3-CH₂=CHC(O)-N(CH₂)₂N-C₆H₄] displayed significant anti-proliferative activity on the Gefitinib-resistant cell line NCI-H1975, with an IC₅₀ value of 0.179μM and 0.173μM, resp. Also, these compounds exhibited moderate anti-proliferative activity against the A549 cell, with an IC₅₀ of 0.550μM and 0.528μM resp., suggesting their improved selectivity over the mutant EGFR-L858R/T790M. Excitingly, both these compounds showed significant inhibition of the double mutant EGFR-L858R/T790M TK with an IC₅₀ value of 0.0063μM and 0.0060μM, resp. The IC₅₀ values of both the promising compounds against the HepG2 cell line were more than 1μM, indicating safety for normal cells. Covalent docking and MD simulation further confirm their irreversible binding mode with the target protein. These results demonstrate that compounds I [R¹ = 4-chloro-3-fluorophenyl, 4-bromophenyl; R² = 3-CH₂=CHC(O)-N(CH₂)₂N-C₆H₄] would be promising lead compound-targeting double mutant EGFR-L858R/T790M TK.

Journal of Molecular Structure published new progress about 67914-60-7. 67914-60-7 belongs to piperazines, auxiliary class Piperazine,Benzene,Phenol,Amide, name is 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone, and the molecular formula is C12H16N2O2, SDS of cas: 67914-60-7.

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

Bayrak, Riza published the artcileSubstituted phthalocyanines and their electropolymerization properties, HPLC of Formula: 67914-60-7, the publication is Synthetic Metals (2016), 643-652, database is CAplus.

New metal-free and metallo-phthalocyanine complexes (Co, TiO) were synthesized using a piperazine-substituted phthalonitrile derivative All proposed structures were supported by instrumental methods. Electrochem. studies of H₂-Pc, Ti^IVOPc, and Co^IIPc were examined using cyclic voltammetry (CV) and square-wave voltammetry (SWV) techniques. Voltammetric analyses of phthalocyanines supported the proposed structure of the synthesized complexes. All studied phthalocyanines were oxidatively electropolymerized on the working electrode during the repetitive anodic potential scans.

Synthetic Metals published new progress about 67914-60-7. 67914-60-7 belongs to piperazines, auxiliary class Piperazine,Benzene,Phenol,Amide, name is 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone, and the molecular formula is C12H16N2O2, HPLC of Formula: 67914-60-7.

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

Nematollahi, Davood published the artcileElectrochemical synthesis of the new substituted phenylpiperazines, Recommanded Product: 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone, the publication is Journal of Electroanalytical Chemistry (2011), 651(1), 72-79, database is CAplus.

Electrochem. oxidation of 1-(4-(4-hydroxyphenyl)piperazin-1-yl)ethanone (1) has been studied in the presence of arylsulfinic acids (3a-c) as nucleophiles in aqueous solutions using cyclic voltammetry and controlled-potential coulometry methods. The results revealed that quinone-imine derived from oxidation of 1 participates in Michael type addition reaction with arylsulfinic acids and via an EC mechanism converts to the corresponding new phenylpiperazine derivatives The present work has led to the development of a facile and environmentally friendly reagent-less electrochem. method for synthesis of some new phenylpiperazine derivatives in aqueous solutions with high atom economy and safe waste under ambient conditions and in an undivided cell using a carbon electrode.

Journal of Electroanalytical Chemistry published new progress about 67914-60-7. 67914-60-7 belongs to piperazines, auxiliary class Piperazine,Benzene,Phenol,Amide, name is 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone, and the molecular formula is C12H16N2O2, Recommanded Product: 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone.

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

O’Boyle, Niamh M. published the artcileSynthesis and evaluation of antiproliferative microtubule-destabilising combretastatin A-4 piperazine conjugates, Recommanded Product: (E)-1-Cinnamylpiperazine, the publication is Organic & Biomolecular Chemistry (2019), 17(25), 6184-6200, database is CAplus and MEDLINE.

Design, synthesis, biochem. evaluation and mol. modeling studies were described for the series of analogs of the microtubule-destabilizing agent, combretastatin A-4 (CA-4) I [R¹ = H, OH, OMe, NO₂, F; R² = OH, OMe; R³ = OH, piperazin-1-yl, 1,4-diazepan-1-yl, etc.] and II [R⁴ = H, OH; R⁵ = OH, piperazin-1-yl, 4-phenylpiperazin-1-yl, etc.] contain the CA-4 core structure with modifications to the stilbene linking group, and were predominantly piperazine derivatives Synthesis was achieved in a two-step process by firstly obtaining the acrylic acid via a Perkin reaction using microwave enhanced synthesis, followed by coupling using either DCC or Mukaiyama’s reagent. All target compounds I and II were screened for antiproliferative activity in MCF-7 breast cancer cells, among them compounds, I [R¹ = OH; R² = OMe, R³ = 4-phenylpiperazin-1-yl] displayed potent antiproliferative activity (IC₅₀ = 190 nM). Two amino-containing derivatives, I [R¹ = NH₂; R² = OMe; R³ = 4-benzylpiperazin-1-yl, 4-(p-tolyl)piperazin-1-yl] were the most potent with IC₅₀ values of 130 nM and 83 nM resp. Representative compounds were shown to depolymerize tubulin, induce G2/M arrest and apoptosis in MCF-7 cells but not peripheral blood mononuclear cells and induce cleavage of the DNA repair enzyme poly ADP ribose polymerase (PARP) in MCF-7 cells. Modeling studies predicted that the compounds I and II bind to tubulin within the colchicine-binding site.

Organic & Biomolecular Chemistry published new progress about 87179-40-6. 87179-40-6 belongs to piperazines, auxiliary class Benzenes, name is (E)-1-Cinnamylpiperazine, and the molecular formula is C13H18N2, Recommanded Product: (E)-1-Cinnamylpiperazine.

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

Malgorzata, Kostecka published the artcileSynthesis and antifungal activity of new series of compounds against Ascosphaera apis, SDS of cas: 87179-40-6, the publication is Organic Chemistry: An Indian Journal (2010), 6(4), 284-292, database is CAplus.

The fungicidal compounds synthesized by us and applied in the studies are: 3,1-benzothiazine, variously substituted thioamides, N-heterocyclic carbothionyl derivatives and 2,5-disubstituted 1,3,4-thiadiazoles. Depending on their structure, their action can be oriented towards zoo- and geophilic fungi that destroy crops and raw material of vegetation origin as well as pathogenic for animals and man. The compounds are characterized by differentiated mechanism of mol. interactions in energetic cell processes and disubstituted 1,3,4-thiadiazole inhibiting squale epoxidase and squale accumulation seem to be an interesting group. Selective estimation of action of some compounds from individual groups against the strain Ascosphaera apis of the fungus isolated from insects infected with calciferous mycosis was made.

Organic Chemistry: An Indian Journal published new progress about 87179-40-6. 87179-40-6 belongs to piperazines, auxiliary class Benzenes, name is (E)-1-Cinnamylpiperazine, and the molecular formula is C13H18N2, SDS of cas: 87179-40-6.

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

Ghosh, Balaram published the artcileFurther delineation of hydrophobic binding sites in dopamine D₂/D₃ receptors for N-4 substituents on the piperazine ring of the hybrid template 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-2-ol, Product Details of C16H18N2, the publication is Bioorganic & Medicinal Chemistry (2010), 18(15), 5661-5674, database is CAplus and MEDLINE.

Here we report a structure-activity relationship (SAR) study of analogs of 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-2-ol. Our SAR is focused on introduction of various substitutions in the piperazine ring of the hybrid template. The goal behind this study is to delineate the nature of the binding pocket for N-aryl substitution in the piperazine ring by observing the effect of various hydrophobic and other heteroaromatic substitutions on binding affinity (K _i), as measured with tritiated spiperone and HEK-293 cells expressing either D₂ or D₃ receptors. Functional activity of selected compounds was assessed with the GTPγS binding assay. Compound I was the most selective for the D₃ receptor in the spiperone binding assay. An interesting similarity in binding affinity was observed between isoquinoline derivative D-301 and the 2-substituted pyridine derivative I, suggesting the importance of relative spatial relationships between the N-atom of the ligand and the mol. determinants of the binding pocket in D₂/D₃ receptors. Functional activity assays demonstrated high potency and selectivity of (+)-II (R¹ = H, R² = OH) and (-)-II (R¹ = OH, R² = H) (D₂/D₃ (ratio of EC₅₀): 105 and 202, resp.) for the D₃ receptor and both compounds were more selective compared to the reference drug ropinirole (D₂/D₃ (ratio of EC₅₀): 29.5).

Bioorganic & Medicinal Chemistry published new progress about 180698-19-5. 180698-19-5 belongs to piperazines, auxiliary class Piperazine,Benzene, name is 1-Biphenyl-4-yl-piperazine, and the molecular formula is C16H18N2, Product Details of C16H18N2.

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

Johnson, Mark published the artcileStructure-Activity Relationship Study of N⁶-(2-(4-(1H-Indol-5-yl)piperazin-1-yl)ethyl)-N⁶-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine Analogues: Development of Highly Selective D3 Dopamine Receptor Agonists along with a Highly Potent D2/D3 Agonist and Their Pharmacological Characterization, SDS of cas: 945953-41-3, the publication is Journal of Medicinal Chemistry (2012), 55(12), 5826-5840, database is CAplus and MEDLINE.

In our effort to develop multifunctional drugs against Parkinson’s disease, a structure-activity-relationship study was carried out based on our hybrid mol. template targeting D2/D3 receptors. Competitive binding with [³H]spiroperidol was used to evaluate affinity (K_i) of test compounds Functional activity of selected compounds in stimulating [³⁵S]GTPγS binding was assessed in CHO cells expressing either human D2 or D3 receptors. Our results demonstrated development of highly selective compounds for D3 receptor (for (-)-40 (I) K_i, D3 = 1.84 nM, D2/D3 = 583.2; for (-)-45K_i, D3 = 1.09 nM, D2/D3 = 827.5). Functional data identified (-)-40 (EC₅₀, D2 = 114 nM, D3 = 0.26 nM, D2/D3 = 438) as one of the highest D3 selective agonists known to date. In addition, high affinity, nonselective D3 agonist (-)-19 (EC₅₀, D2 = 2.96 nM and D3 = 1.26 nM) was also developed. Lead compounds with antioxidant activity were evaluated using an in vivo PD animal model.

Journal of Medicinal Chemistry published new progress about 945953-41-3. 945953-41-3 belongs to piperazines, auxiliary class Piperazine,Amide,Aldehyde, name is tert-Butyl 4-(2-oxoethyl)piperazine-1-carboxylate, and the molecular formula is C11H20N2O3, SDS of cas: 945953-41-3.

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