Month: January 2023

Quinoxalinone inhibitors of the lectin DC-SIGN was written by Mangold, Shane L.;Prost, Lynne R.;Kiessling, Laura L.. And the article was included in Chemical Science in 2012.Reference of 21867-64-1 This article mentions the following:

The C-type lectin dendritic cell-specific intercellular adhesion mol. 3-grabbing nonintegrin (DC-SIGN) can serve as a docking site for pathogens on the surface of dendritic cells. Pathogen binding to DC-SIGN can have diverse consequences for the host. DC-SIGN can facilitate HIV-1 dissemination, but the interaction of Mycobacterium tuberculosis with DC-SIGN is important for host immunity. The ability of pathogens to target DC-SIGN provides impetus to identify ligands that can perturb these interactions. Here, we describe the first stable small mol. inhibitors of DC-SIGN. These inhibitors were derived from a collection of quinoxalinones, which were assembled using a tandem cross metathesis-hydrogenation sequence. To assess the ability of these small mols. to block DC-SIGN-mediated glycan adhesion and internalization, we developed a sensitive flow cytometry assay. Our results reveal that the quinoxalinones are effective inhibitors of DC-SIGN-glycan interactions. These compounds block both glycan binding to cells and glycan internalization. We anticipate that these non-carbohydrate inhibitors can be used to elucidate the role of DC-SIGN in pathogenesis and immune function. In the experiment, the researchers used many compounds, for example, 1-Propylpiperazine (cas: 21867-64-1Reference of 21867-64-1).

1-Propylpiperazine (cas: 21867-64-1) belongs to piperazine derivatives. Industrial applications of piperazine include the manufacture of plastics, resins, pesticides and brake fluids. Outside the body, piperazine has a remarkable power to dissolve uric acid and producing a soluble urate, but in clinical experience it has not proved equally successful. Reference of 21867-64-1

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Synthesis and cytotoxicity evaluation of (tetrahydro-β-carboline)-1,3,5-triazine hybrids as anticancer agents was written by Kumar, Ravi;Gupta, Leena;Pal, Pooja;Khan, Shahnawaz;Singh, Neetu;Katiyar, Sanjay Babu;Meena, Sanjeev;Sarkar, Jayanta;Sinha, Sudhir;Kanaujiya, Jitendra Kumar;Lochab, Savita;Trivedi, Arun Kumar;Chauhan, Prem M. S.. And the article was included in European Journal of Medicinal Chemistry in 2010.Electric Literature of C7H16N2 This article mentions the following:

A series of tetrahydro-β-carbolines and 1,3,5-triazine hybrids have been synthesized and evaluated for their cytotoxicity against a panel of eight human cancer cell lines and normal human fibroblasts (NIH3T3). It led us to discovery of three racemic compounds which are selectively cytotoxic towards KB (oral cancer) cell line with IC₅₀ values of 105.8, 664.7 and 122.2 nM, resp.; their enantiopure forms are less active and not selective. Enantiopure compound I (R = N-methylpiperazine) showed 2.5 times more selectivity towards MCF7 cells over normal fibroblast NIH3T3 cells with an IC₅₀ value of 740 nM, also arrests cell cycle in G₁ phase and induces apoptosis in MCF7 and MDA MB231cell lines. In the experiment, the researchers used many compounds, for example, 1-Propylpiperazine (cas: 21867-64-1Electric Literature of C7H16N2).

1-Propylpiperazine (cas: 21867-64-1) belongs to piperazine derivatives. Piperazine is a fairly basic compound and is an amine solvent. Outside the body, piperazine has a remarkable power to dissolve uric acid and producing a soluble urate, but in clinical experience it has not proved equally successful. Electric Literature of C7H16N2

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Synthesis and polymerization of active ester monomers based on 4-vinylbenzoic acid was written by Nilles, Katja;Theato, Patrick. And the article was included in European Polymer Journal in 2007.Name: 1-Propylpiperazine This article mentions the following:

Nine active ester monomers based on 4-vinylbenzoic acid have been synthesized. Under free radical polymerization conditions these monomers could successfully be polymerized yielding reactive polymers with mol. weights of around M_n = 20.000-50.000 g/mol and mol. weight distributions M_w/M_n of around or below 2 in good yields. Polymer analogous reactions with amines have been investigated by time-resolved FT-IR spectroscopy and it was found that especially poly(pentafluorophenyl 4-vinylbenzoate) featured a significant reactivity, such that polymer analogous reactions proceeded quant. with amines within less than 5 min at 0°. In the experiment, the researchers used many compounds, for example, 1-Propylpiperazine (cas: 21867-64-1Name: 1-Propylpiperazine).

1-Propylpiperazine (cas: 21867-64-1) belongs to piperazine derivatives. Piperazine causes primary dermal irritation and skin burns at high concentrations. Piperazine also causes eye irritation in humans. Piperazine is formed as a co-product in the ammoniation of 1,2-dichloroethane or ethanolamine. These are the only routes to the chemical used commercially.Name: 1-Propylpiperazine

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Hitting a Moving Target: Simulation and Crystallography Study of ATAD2 Bromodomain Blockers was written by Dolbois, Aymeric;Batiste, Laurent;Wiedmer, Lars;Dong, Jing;Brutsch, Manuela;Huang, Danzhi;Deerain, Nicholas M.;Spiliotopoulos, Dimitrios;Cheng-Sanchez, Ivan;Laul, Eleen;Nevado, Cristina;Sledz, Pawel;Caflisch, Amedeo. And the article was included in ACS Medicinal Chemistry Letters in 2020.Name: 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid This article mentions the following:

Small mol. ligand binding to the ATAD2 bromodomain is investigated here through the synergistic combination of mol. dynamics and protein crystallog. A previously unexplored conformation of the binding pocket upon rearrangement of the gatekeeper residue Ile1074 has been found. Further, our investigations reveal how minor structural differences in the ligands result in binding with different plasticity of the ZA loop for this difficult-to-drug bromodomain. In the experiment, the researchers used many compounds, for example, 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (cas: 149057-19-2Name: 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid).

4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (cas: 149057-19-2) belongs to piperazine derivatives. Piperazine was first introduced as an anthelmintic in 1953. Piperazine compounds mediate their anthelmintic action by generally paralyzing parasites, allowing the host body to easily remove or expel the invading organism. Although many piperazine derivatives occur naturally, piperazine itself can be synthesized by reacting alcoholic ammonia with 1,2-dichloroethane, by the action of sodium and ethylene glycol on ethylene diamine hydrochloride, or by reduction of pyrazine with sodium in ethanol.Name: 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Expanding Reactivity in DNA-Encoded Library Synthesis via Reversible Binding of DNA to an Inert Quaternary Ammonium Support was written by Flood, Dillon T.;Asai, Shota;Zhang, Xuejing;Wang, Jie;Yoon, Leonard;Adams, Zoe C.;Dillingham, Blythe C.;Sanchez, Brittany B.;Vantourout, Julien C.;Flanagan, Mark E.;Piotrowski, David W.;Richardson, Paul;Green, Samantha A.;Shenvi, Ryan A.;Chen, Jason S.;Baran, Phil S.;Dawson, Philip E.. And the article was included in Journal of the American Chemical Society in 2019.Electric Literature of C16H22N2O4 This article mentions the following:

DNA Encoded Libraries have proven immensely powerful tools for lead identification. The ability to screen billions of compounds at once has spurred increasing interest in DEL development and utilization. Although DEL provides access to libraries of unprecedented size and diversity, the idiosyncratic and hydrophilic nature of the DNA tag severely limits the scope of applicable chemistries. It is known that biomacromols. can be reversibly, noncovalently adsorbed and eluted from solid supports, and this phenomenon has been utilized to perform synthetic modification of biomols. in a strategy we have described as reversible adsorption to solid support (RASS). Herein, we present the adaptation of RASS for a DEL setting, which allows reactions to be performed in organic solvents at near anhydrous conditions opening previously inaccessible chem. reactivities to DEL. The RASS approach enabled the rapid development of C(sp²)-C(sp³) decarboxylative cross-couplings with broad substrate scope, an electrochem. amination (the first electrochem. synthetic transformation performed in a DEL context), and improved reductive amination conditions. The utility of these reactions was demonstrated through a DEL-rehearsal in which all newly developed chemistries were orchestrated to afford a compound rich in diverse skeletal linkages. We believe that RASS will offer expedient access to new DEL reactivities, expanded chem. space, and ultimately more drug-like libraries. In the experiment, the researchers used many compounds, for example, 4-(4-(tert-Butoxycarbonyl)piperazin-1-yl)benzoic acid (cas: 162046-66-4Electric Literature of C16H22N2O4).

4-(4-(tert-Butoxycarbonyl)piperazin-1-yl)benzoic acid (cas: 162046-66-4) belongs to piperazine derivatives. Piperazine belongs to the family of medicines called anthelmintics. Outside the body, piperazine has a remarkable power to dissolve uric acid and producing a soluble urate, but in clinical experience it has not proved equally successful. Electric Literature of C16H22N2O4

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Falcipain Inhibitors: Optimization Studies of the 2-Pyrimidinecarbonitrile Lead Series was written by Coteron, Jose M.;Catterick, David;Castro, Julia;Chaparro, Maria J.;Diaz, Beatriz;Fernandez, Esther;Ferrer, Santiago;Gamo, Francisco J.;Gordo, Mariola;Gut, Jiri;de las Heras, Laura;Legac, Jennifer;Marco, Maria;Miguel, Juan;Munoz, Vicente;Porras, Esther;de la Rosa, Juan C.;Ruiz, Jose R.;Sandoval, Elena;Ventosa, Pilar;Rosenthal, Philip J.;Fiandor, Jose M.. And the article was included in Journal of Medicinal Chemistry in 2010.Reference of 21867-64-1 This article mentions the following:

Falcipain-2 and falcipain-3 are papain-family cysteine proteases of the malaria parasite Plasmodium falciparum that are responsible for host Hb hydrolysis to provide amino acids for parasite protein synthesis. Different heteroarylnitrile derivatives were studied as potential falcipain inhibitors and therefore potential antiparasitic lead compounds, with the 5-substituted-2-cyanopyrimidine chem. class emerging as the most potent and promising lead series. Through a sequential lead optimization process considering the different positions present in the initial scaffold, nanomolar and subnanomolar inhibitors at falcipains 2 and 3 were identified, with activity against cultured parasites in the micromolar range. Introduction of protonable amines within lead mols. led to marked improvements of up to 1000 times in activity against cultured parasites without noteworthy alterations in other SAR tendencies. Optimized compounds presented enzymic activities in the picomolar to low nanomolar range and antiparasitic activities in the low nanomolar range. In the experiment, the researchers used many compounds, for example, 1-Propylpiperazine (cas: 21867-64-1Reference of 21867-64-1).

1-Propylpiperazine (cas: 21867-64-1) belongs to piperazine derivatives. Simple N-substituted piperazines have been found in many drug molecules. Although many piperazine derivatives occur naturally, piperazine itself can be synthesized by reacting alcoholic ammonia with 1,2-dichloroethane, by the action of sodium and ethylene glycol on ethylene diamine hydrochloride, or by reduction of pyrazine with sodium in ethanol.Reference of 21867-64-1

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

SAR studies on a series of N-benzyl-4-heteroaryl-1-(phenylsulfonyl)piperazine-2-carboxamides: Potent inhibitors of the polymerase enzyme (NS5B) of the hepatitis C virus was written by Gentles, Robert G.;Ding, Min;Zheng, Xiaofan;Chupak, Louis;Poss, Michael A.;Beno, Brett R.;Pelosi, Lenore;Liu, Mengping;Lemm, Julie;Wang, Ying-Kai;Roberts, Susan;Gao, Min;Kadow, John. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Name: 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid This article mentions the following:

Described herein is the initial optimization of (+/-) N-benzyl-4-heteroaryl-1-(phenylsulfonyl)piperazine-2-carboxamide (1)(I), a hit discovered in a high throughput screen run against the NS5B polymerase enzyme of the hepatitis C virus. This effort resulted in the identification of (S)-N-sec-butyl-6-((R)-3-(4-(trifluoromethoxy)benzylcarbamoyl)-4-(4-(trifluoromethoxy)phenylsulfonyl)piperazin-1-yl)pyridazine-3-carboxamide (2)(II), that displayed potent replicon activities against HCV genotypes 1b and 1a (EC₅₀ 1b/1a = 7/89 nM). In the experiment, the researchers used many compounds, for example, 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (cas: 149057-19-2Name: 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid).

4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (cas: 149057-19-2) belongs to piperazine derivatives. Piperazine belongs to the family of medicines called anthelmintics. Intermediate for a wide range of pharmaceuticals, polymers, dyes, corrosion inhibitors, rubber accelerators and surfactants.Name: 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Discovery of Potent and Orally Effective Dual Janus Kinase 2/FLT3 Inhibitors for the Treatment of Acute Myelogenous Leukemia and Myeloproliferative Neoplasms was written by Yang, Tao;Hu, Mengshi;Qi, Wenyan;Yang, Zhuang;Tang, Minghai;He, Jun;Chen, Yong;Bai, Peng;Yuan, Xue;Zhang, Chufeng;Liu, Kongjun;Lu, Yulin;Xiang, Mingli;Chen, Lijuan. And the article was included in Journal of Medicinal Chemistry in 2019.Formula: C15H21N3O4 This article mentions the following:

Herein, the design, synthesis, and structure-activity relationships of a series of unique 4-(1H-pyrazol-4-yl)-pyrimidin-2-amine derivatives that selectively inhibit Janus kinase 2 (JAK2) and FLT3 kinases is described. These screening cascades revealed that I was a preferred compound with IC₅₀ values of 0.7 and 4 nM for JAK2 and FLT3, resp. Moreover, I was a potent JAK2 inhibitor with 37-fold and 56-fold selectivity over JAK1 and JAK3, resp., and possessed an excellent selectivity profile over the other 100 representative kinases. In a series of cytokine-stimulated cell-based assays, I exhibited a higher JAK2 selectivity over other JAK isoforms. The oral administration of 60 mg/kg of I could significantly inhibit tumor growth, with a tumor growth inhibition rate of 93 and 85% in MV4-11 and SET-2 xenograft models, resp. Addnl., I showed an excellent bioavailability (F = 58%), a suitable half-life time (T_1/2 = 4.1 h), a satisfactory metabolic stability, and a weak CYP3A4 inhibitory activity, suggesting that I might be a potential drug candidate for JAK2-driven myeloproliferative neoplasms and FLT3-internal tandem duplication-driven acute myelogenous leukemia. In the experiment, the researchers used many compounds, for example, 1-Boc-4-(4-Nitrophenyl)piperazine (cas: 182618-86-6Formula: C15H21N3O4).

1-Boc-4-(4-Nitrophenyl)piperazine (cas: 182618-86-6) belongs to piperazine derivatives. Simple N-substituted piperazines have been found in many drug molecules. Piperazine and its salts did not induce point mutations in a bacterial test. A series of mutagenicity studies in cells, both in vitro and in vivo, has been completed and showed no evidence of mutagenic effect.Formula: C15H21N3O4

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Identification and SAR of novel pyrrolo[1,2-a]pyrazin-1(2H)-one derivatives as inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1) was written by Pescatore, Giovanna;Branca, Danila;Fiore, Fabrizio;Kinzel, Olaf;Bufi, Laura Llauger;Muraglia, Ester;Orvieto, Federica;Rowley, Michael;Toniatti, Carlo;Torrisi, Caterina;Jones, Philip. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.Formula: C10H12N4 This article mentions the following:

The discovery of a novel series of pyrrolo[1,2-a]pyrazin-1(2H)-one PARP inhibitors is described. Optimization led to compounds that display excellent PARP-1 enzyme potency and inhibit the proliferation of BRCA deficient cells in the low double-digit nanomolar range showing excellent selectivity over BRCA proficient cancer cells. In the experiment, the researchers used many compounds, for example, 6-(Piperazin-1-yl)nicotinonitrile (cas: 149554-29-0Formula: C10H12N4).

6-(Piperazin-1-yl)nicotinonitrile (cas: 149554-29-0) belongs to piperazine derivatives. Piperazine was first introduced as an anthelmintic in 1953. Piperazine compounds mediate their anthelmintic action by generally paralyzing parasites, allowing the host body to easily remove or expel the invading organism. Outside the body, piperazine has a remarkable power to dissolve uric acid and producing a soluble urate, but in clinical experience it has not proved equally successful. Formula: C10H12N4

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Falcipain Inhibitors: Optimization Studies of the 2-Pyrimidinecarbonitrile Lead Series. [Erratum to document cited in CA153:382905] was written by Coteron, Jose M.;Catterick, David;Castro, Julia;Chaparro, Maria J.;Diaz, Beatriz;Fernandez, Esther;Ferrer, Santiago;Gamo, Francisco J.;Gordo, Mariola;Gut, Jiri;de las Heras, Laura;Legac, Jennifer;Marco, Maria;Miguel, Juan;Munoz, Vicente;Porras, Esther;de la Rosa, Juan C.;Ruiz, Jose R.;Sandoval, Elena;Ventosa, Pilar;Rosenthal, Philip J.;Fiandor, Jose M.. And the article was included in Journal of Medicinal Chemistry in 2010.Synthetic Route of C7H16N2 This article mentions the following:

On page 6143, Table 12 is incorrect; the corrections to the table are given. On page S7, in Table S6, the structure for compound 144 is incorrect. On pages S29, S34, S36, S38-39, Table S9 is incorrect; the corrections to the Table are given. In the experiment, the researchers used many compounds, for example, 1-Propylpiperazine (cas: 21867-64-1Synthetic Route of C7H16N2).

1-Propylpiperazine (cas: 21867-64-1) belongs to piperazine derivatives. Piperazine is a fairly basic compound and is an amine solvent. Two common salts in the form of which piperazine is usually prepared for pharmaceutical or veterinary purposes are the citrate, 3C4H10N2.2C6H8O7 (i.e. containing 3 molecules of piperazine to 2 molecules of citric acid), and the adipate, C4H10N2.C6H10O4 (containing 1 molecule each of piperazine and adipic acid).Synthetic Route of C7H16N2

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics