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Cas Database

118591-58-5

118591-58-5

Identification

Synonyms:2-(2-hydroxyethoxy)ethyl 4-methyl benzenesulfonate;Ethanol,2-(2-hydroxyethoxy)-,1-(4-Methylbenzenesulfonate);Ts(OCH2CH2)2OH;2-(2-{[(4-methylbenzene)sulfonyl]oxy}ethoxy)ethan-1-ol;2-(2-hydroxyethoxy)ethyl p-methylbenzenesulfonate;toluene-4-sulfonic acid 2-(2-hydroxyethoxy)ethyl ester;diethylene glycol mono-p-toluenesulfonate;

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Relevant articles and documentsAll total 62 Articles be found

Clickable prodrugs bearing potent and hydrolytically cleavable nicotinamide phosphoribosyltransferase inhibitors

Sadrerafi, Keivan,Mason, Emilia O.,Lee, Mark W.

, p. 987 - 995 (2018)

Purpose: Our previous study indicated that carborane containing small-molecule 1-(hydroxymethyl)-7-(4′-(trans-3″-(3′″-pyridyl)acrylamido)butyl)-1,7-dicarbadodecaborane (hm-MC4-PPEA), was a potent inhibitor of nicotinamide phosphoribosyltransferase (Nampt)

Synthesis and antitumor activity of DNA binding cationic porphyrin-platinum(II) complexes

Song, Rita,Kim, Yeong-Sang,Lee, Chong Ock,Sohn, Youn Soo

, p. 1537 - 1540 (2003)

A new series of DNA binding 5,10,15-tri(N-methyl-4-pyridiniumyl)porphyrin (TrisMPyP)-platinum(II) conjugates was synthesized, in which different spacer ligands were used for appropriate coordination to platinum(II) complexes. Compound 9b exhibited in vivo antitumor activity (T/C%, 294) superior to cisplatin (T/C%, 184) against the leukemia L1210 cell line.

Gold nanoparticles coated with semi-fluorinated oligo(ethylene glycol) produce sub-100 nm nanoparticle vesicles without templates

Niikura, Kenichi,Iyo, Naoki,Higuchi, Takeshi,Nishio, Takashi,Jinnai, Hiroshi,Fujitani, Naoki,Ijiro, Kuniharu

, p. 7632 - 7635 (2012)

Gold nanoparticles (NPs) with diameters of 5, 10, and 20 nm coated with semifluorinated oligo(ethylene glycol) ligands were formed into sub-100 nm hollow NP assemblies (NP vesicles) in THF without the use of a template. The NP vesicles maintained their st

Stable pillar[5]arene-based pseudo[1]rotaxanes formed in polar solution

Wu, Xuan,Gao, Lei,Sun, Junzhao,Hu, Xiao-Yu,Wang, Leyong

, p. 1655 - 1660 (2016)

Mono-alkyl-functionalized pillar[5]arenes P1, P2, and P3 were synthesized by click reaction, which exhibited different self-assembly behavior in polar solvent DMSO. Stable pseudo[1]rotaxane was formed by the self-complexation from P1 or P2, whereas, concentration-dependent pseudorotaxane structures were generated by P3 which bearing more flexible side chain. Interestingly, the obtained pseudo[1]rotaxanes exhibited a dynamic fast assembly process upon adding NaBF4, resulting in the formation of Na+-induced pseudorotaxanes.

Synthesis of optically active 1,1′-binaphthyl-phthalocyanines linked via a crown ether unit

Liu, Hong-Wei,Chen, Chuan-Fu,Ai, Min,Gong, Ai-Jun,Jiang, Jing,Xi, Fu

, p. 4915 - 4922 (2000)

Novel optically active metal and metal-free phthalocyanines, substituted with 1,1′-binaphthyl crown ether units, have been synthesized and characterized.

Pegylated triarylmethanes: Synthesis, antimicrobial activity, anti-proliferative behavior and in silico studies

Abdmouleh, Fatma,Ali, Mamdouh Ben,Arbi, Mehdi El,Ferroud, Clotilde,Goya-Jorge, Elizabeth,Guenineche, Léna,Lagarde, Nathalie,Liagre, Bertrand,Martin, Frédérique,Ricco, Christophe,Riccobono, Charlotte,Veitía, Maité Sylla-Iyarreta

, (2020)

We describe herein the synthesis, characterization and biological studies of novel PEGylated triarylmethanes. Non-symmetrical and symmetrical triarylmethanes series have been synthesized by Friedel-Crafts hydroxyalkylation or directly from bisacodyl respectively followed by a functionalization with PEG fragments in order to increase bioavailability and biological effectiveness. The antimicrobial activity was investigated against Gram-positive and Gram-negative foodborne pathogens and against Candida albicans, an opportunistic pathogenic yeast. The anti-biocidal activity was also studied using Staphylococcus aureus as a reference bacterium. Almost all PEGylated molecules displayed an antifungal activity comparable with fusidic acid with MIC values ranging from 6.25 to 50 μg/mL. Compounds also revealed a promising antibiofilm activity with biofilm eradication percentages values above 80% for the best molecules (compounds 4d and 7). Compounds 7 and 8b showed a modest antiproliferative activity against human colorectal cancer cell lines HT-29. Finally, in silico molecular docking studies revealed DHFR and DNA gyrase B as potential anti-bacterial targets and in silico predictions of ADME suggested adequate drug-likeness profiles for the synthetized triarylmethanes.

Closing the Loop: Triazolylpyridine Coordination Drives the Self-Assembly of Metallomacrocycles with Tunable Topologies for Small-Molecule and Guanine-Quadruplex Recognition

Miron, Caitlin E.,Colden Leung, Madelaine R.,Kennedy, Emily I.,Fleischel, Olivier,Khorasani, Mona Ashraf,Wu, Nan,Mergny, Jean-Louis,Petitjean, Anne

, p. 18718 - 18734 (2018)

The 2-(1,2,3-triazol-4-yl)pyridine motif, with its facile “click” synthesis and remarkable coordinative properties, is an attractive chelate for applications in the metal-directed self-assembly of intricate three-dimensional structures. Organic ligands th

Discovery of a new class of PROTAC BRD4 degraders based on a dihydroquinazolinone derivative and lenalidomide/pomalidomide

Zhang, Fangqing,Wu, Zhenwei,Chen, Pan,Zhang, Jian,Wang, Tao,Zhou, Jinpei,Zhang, Huibin

, (2020)

BRD4 has emerged as an attractive target for anticancer therapy. However, BRD4 inhibitors treatment leads to BRD4 protein accumulation, together with the reversible nature of inhibitors binding to BRD4, which may limit the efficacy of BRD4 inhibitors. To address these problems, a protein degradation strategy based on the proteolysis targeting chimera (PROTAC) technology has been developed to target BRD4 recently. Herein, we present our design, synthesis and biological evaluation of a new class of PROTAC BRD4 degraders, which were based on a potent dihydroquinazolinone-based BRD4 inhibitor compound 6 and lenalidomide/pomalidomide as ligand for E3 ligase cereblon. Gratifyingly, several compounds showed excellent inhibitory activity against BRD4, and high anti-proliferative potency against human monocyte lymphoma cell line THP-1. Especially, compound 21 (BRD4 BD1, IC50 = 41.8 nM) achieved a submicromolar IC50 value of 0.81 μM in inhibiting the growth of THP-1 cell line, and was 4 times more potent than compound 6. Moreover, the mechanism study established that 21 could effectively induce the degradation of BRD4 protein and suppression of c-Myc. All of these results suggested that 21 was an efficacious BRD4 degrader for further investigation.

SYNTHESIS OF 2-(2-AMINOETHOXY) ETHANOL

-

Paragraph 0055-0057, (2021/02/12)

A method for synthesizing 2-(2-aminoethoxy) ethanol, including the steps of producing 2-(2-phthalimidoethoxy) ethanol by reacting 5-tosyloxy-3-oxapentanol with potassium phthalate and converting the 2-(2-phthalimidoethoxy) ethanol to the 2-(2-aminoethoxy) ethanol by reacting the 2-(2-phthalimidoethoxy) ethanol with hydrazine monohydrate. Reacting the 2-(2-phthalimidoethoxy) ethanol with the hydrazine monohydrate may include forming a final mixture by adding the hydrazine monohydrate to a solution of 2-(2-phthalimidoethoxy) ethanol, refluxing the final mixture in a nitrogen atmosphere, extracting a second organic phase containing the 2-(2-aminoethoxy) ethanol from the final mixture using a second portion of chloroform, and purifying the 2-(2-aminoethoxy) ethanol from the second organic phase.

Fluorescent Columnar Liquid-Crystalline Polymers: Synthesis, Mesomorphic Behaviors and Tunable Emission Wavelengths?

Hao, Xiangnan,Mu, Bin,Tian, Wei,Zhang, Zhelin,Zhao, Yu

supporting information, p. 2009 - 2015 (2021/06/08)

Fluorescent columnar liquid-crystalline polymers have attracted intensive attention due to their unique features that can be applied in many fields. However, the utilization of molecular engineering to achieve efficient fluorescence tuning has rarely been

Synthesis, biological evaluation and QSAR studies of new thieno[2,3-d]pyrimidin-4(3H)-one derivatives as antimicrobial and antifungal agents

Magoulas, George E.,Kalopetridou, Lefkothea,?iri?, Ana,Kritsi, Eftichia,Kouka, Paraskevi,Zoumpoulakis, Panagiotis,Chondrogianni, Niki,Sokovi?, Marina,Prousis, Kyriakos C.,Calogeropoulou, Theodora

, (2020/12/13)

A series of new thieno[2,3-d]pyrimidin-4(3H)-one derivatives were synthesized and evaluated for their activity against four gram-positive and four gram-negative bacterial and eight fungal species. The majority of the compounds exhibited excellent antimicr

Supramolecular compound nano-carrier as well as preparation method and application thereof

-

Paragraph 0068; 0082, (2021/08/14)

The invention discloses a supramolecular compound nano-carrier as well as a preparation method and application thereof, and relates to the technical field of polymer chemistry and biological detection engineering. According to the supramolecular compound nano-carrier disclosed by the invention, a two-dimensional nanosheet supramolecular structure system generated by self-assembly is driven by an anion induction effect, and a supramolecular compound nano-carrier is of a single-layer nanosheet supramolecular structure constructed by a highly-oriented one-dimensional nanorod. A hydrophobic perylene group part is used as a skeleton part for constructing the highly-oriented one-dimensional nanorod, and the charge density of a single-layer nanosheet can be regulated and controlled. The surface of the water-soluble multivalent hydrophilic part can be loaded with DNAzyme deoxyribozyme for specific detection of heavy metal ions through electrostatic interaction, and the water-soluble multivalent supramolecular compound nano sensor is constructed. Based on a fluorescence change mechanism caused by specific cutting of heavy metal ions, The fluorescence detection of the heavy metal ions in food and biological tissues is realized, and the detection effect of the heavy metal ions is greatly enhanced.

COMPOUNDS AND USES THEREOF

-

Page/Page column 157, (2021/08/06)

The present disclosure features compounds and methods useful for the treatment of BAF complex-related disorders.

Process route upstream and downstream products

Process route

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

diethylene glycol
111-46-6

diethylene glycol

5-tosyloxy-3-oxapentanol
118591-58-5

5-tosyloxy-3-oxapentanol

Conditions
Conditions Yield
With potassium iodide; silver(l) oxide; In dichloromethane; for 10h;
99%
With silver(II) oxide; potassium iodide; In dichloromethane; at 0 - 20 ℃; for 1h; Darkness;
99%
With triethylamine; In dichloromethane; at 20 ℃; for 24h;
98%
With potassium iodide; silver(l) oxide; In dichloromethane; at 0 - 20 ℃; for 0.5h;
92%
With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 2h; Cooling with ice;
90.6%
With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; Cooling;
90.6%
With sodium hydroxide; In tetrahydrofuran; water; for 6h;
89%
With dmap; triethylamine; In dichloromethane; for 2h; Ambient temperature;
88%
diethylene glycol; With sodium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 0.5h;
p-toluenesulfonyl chloride; In tetrahydrofuran; water;
87%
diethylene glycol; With silver(l) oxide; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
p-toluenesulfonyl chloride; With potassium iodide; In dichloromethane; at 0 ℃; for 4h; Inert atmosphere;
82%
With triethylamine; In dichloromethane; at 20 ℃; for 1h;
82%
diethylene glycol; With sodium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 1h;
p-toluenesulfonyl chloride; In tetrahydrofuran; water; at 0 ℃; for 2h;
79%
With triethylamine; In dichloromethane; at 20 ℃; for 1h;
74%
With triethylamine; In dichloromethane; for 1h; Inert atmosphere;
74%
With triethylamine; In dichloromethane; at 20 ℃; for 24h;
67%
With potassium hydroxide; In tetrahydrofuran; at 20 ℃; for 5h; Cooling with ice;
65%
With sodium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 2h; Microwave irradiation;
63%
With triethylamine; In dichloromethane; at 20 ℃;
60%
With triethylamine; In dichloromethane; at 20 ℃; Cooling with ice;
60%
With potassium iodide; silver(l) oxide; In dichloromethane; at 20 ℃; for 24h;
60%
With triethylamine; In dichloromethane; at 0 ℃; for 3h;
58%
With triethylamine; In dichloromethane; at 0 ℃; for 2h;
56%
With potassium iodide; silver(l) oxide; In dichloromethane; at 20 ℃; for 12h;
56%
diethylene glycol; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;
p-toluenesulfonyl chloride; In tetrahydrofuran; mineral oil; at 0 - 25 ℃; for 6h;
51%
diethylene glycol; With sodium hydroxide; In water; at 0 - 20 ℃;
p-toluenesulfonyl chloride; In tetrahydrofuran; at 0 ℃; for 1.33h;
47%
With triethylamine; In dichloromethane; at 25 ℃; for 12h;
46%
With triethylamine; In dichloromethane; at 20 ℃;
40%
With triethylamine; In dichloromethane; at 25 ℃; for 16h; Inert atmosphere;
40%
With triethylamine; In dichloromethane; at 20 ℃; for 12h; Cooling with ice;
40%
diethylene glycol; With sodium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 0.5h;
p-toluenesulfonyl chloride; In tetrahydrofuran; water; at 0 ℃;
40.26%
In dichloromethane; at 16 ℃; for 18h;
39%
With triethylamine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
36%
With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 4h; Inert atmosphere;
35%
With trimethylamine hydrochloride; triethylamine; In dichloromethane; at 0 - 20 ℃;
32%
With triethylamine; In dichloromethane; for 0.5h; Cooling with ice;
29.5%
With potassium iodide; silver(l) oxide; In dichloromethane; at 0 - 25 ℃; for 1.66667h; Inert atmosphere;
24%
With triethylamine; In dichloromethane; at 40 ℃; for 12h;
22%
With triethylamine; In dichloromethane; at 20 ℃; for 1.5h;
19 g
With sodium hydroxide; In tetrahydrofuran; water;
With triethylamine; In dichloromethane; at 25 ℃; for 1h; Inert atmosphere;
With triethylamine; In dichloromethane; at 25 ℃; for 1h; Inert atmosphere;
With triethylamine; In dichloromethane; at 25 ℃; for 1h; Inert atmosphere;
With pyridine; In dichloromethane; at 0 ℃;
With sodium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 3h;
2.46 g
With triethylamine; In dichloromethane; at 25 ℃; for 1h; Inert atmosphere;
With triethylamine; In dichloromethane; at 25 ℃; for 1h; Inert atmosphere;
With pyridine; at 0 - 20 ℃; Inert atmosphere;
22.7 g
With triethylamine; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere;
With pyridine; at 20 ℃; for 4h;
With triethylamine; In dichloromethane; at 0 - 20 ℃; for 12h;
With triethylamine; In dichloromethane; at 20 ℃; for 24h;
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

diethylene glycol
111-46-6

diethylene glycol

5-tosyloxy-3-oxapentanol
118591-58-5

5-tosyloxy-3-oxapentanol

diethylene glycol ditosylate
7460-82-4

diethylene glycol ditosylate

Conditions
Conditions Yield
With potassium iodide; silver(l) oxide; In dichloromethane; at 0 ℃; for 0.0833333h;
92%
5%
With potassium iodide; silver(l) oxide; In dichloromethane; at 0 ℃; for 4h;
90.6%
4.3%
With potassium iodide; silver(l) oxide; In dichloromethane; at 20 ℃; for 0.0833333h;
15%
79%
With potassium iodide; silver(l) oxide; In dichloromethane; at 0 - 20 ℃; for 6h; Inert atmosphere;
77%
8%
diethylene glycol; With sodium hydroxide; In water; at 20 ℃;
p-toluenesulfonyl chloride; In tetrahydrofuran; water; at 0 ℃; for 1.33333h;
47%
With triethylamine; In dichloromethane; at 20 ℃;
36%
ethylene glycol
107-21-1

ethylene glycol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

5-tosyloxy-3-oxapentanol
118591-58-5

5-tosyloxy-3-oxapentanol

Conditions
Conditions Yield
With triethylamine; In dichloromethane; at 40 ℃; for 12h;
23%
toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

diethylene glycol
111-46-6

diethylene glycol

5-tosyloxy-3-oxapentanol
118591-58-5

5-tosyloxy-3-oxapentanol

Conditions
Conditions Yield
With pyridine; at 20 ℃; for 6h;
29%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

5-tosyloxy-3-oxapentanol
118591-58-5

5-tosyloxy-3-oxapentanol

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: pyridine / dichloromethane / 48 h / 20 °C
2: ethyl acetate; hexane
With pyridine; In hexane; dichloromethane; ethyl acetate;
2-(2-methoxyethoxy)ethyl alcohol
111-77-3,95507-80-5

2-(2-methoxyethoxy)ethyl alcohol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

5-tosyloxy-3-oxapentanol
118591-58-5

5-tosyloxy-3-oxapentanol

Conditions
Conditions Yield
With triethylamine; In dichloromethane;
diethylene glycol ditosylate
7460-82-4

diethylene glycol ditosylate

5-tosyloxy-3-oxapentanol
118591-58-5

5-tosyloxy-3-oxapentanol

Conditions
Conditions Yield
In hexane; ethyl acetate;
0.57 g
5-tosyloxy-3-oxapentanol
118591-58-5

5-tosyloxy-3-oxapentanol

Conditions
Conditions Yield
With potassium iodide; silver(l) oxide; In dichloromethane; at 0 - 20 ℃; for 16h;
61%
With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 4h; Inert atmosphere;
35%
5-tosyloxy-3-oxapentanol
118591-58-5

5-tosyloxy-3-oxapentanol

diethylamine
109-89-7

diethylamine

2-[2-(diethylamino)ethoxy] ethanol
140-82-9

2-[2-(diethylamino)ethoxy] ethanol

Conditions
Conditions Yield
With potassium carbonate; In 1,4-dioxane; at 70 ℃;
42%
phenylmethyl 1-piperazinecarboxylate
31166-44-6

phenylmethyl 1-piperazinecarboxylate

5-tosyloxy-3-oxapentanol
118591-58-5

5-tosyloxy-3-oxapentanol

benzyl 4-(2-(2-hydroxyethoxy)ethyl)piperazine-1-carboxylate

benzyl 4-(2-(2-hydroxyethoxy)ethyl)piperazine-1-carboxylate

Conditions
Conditions Yield
With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃;

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  • Amadis Chemical Co., Ltd.
  • Business Type:Lab/Research institutions
  • Contact Tel:86-571-89925085
  • Emails:sales@amadischem.com
  • Main Products:29
  • Country:China (Mainland)
  • SAGECHEM LIMITED
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-571-86818502
  • Emails:will@sagechem.com
  • Main Products:28
  • Country:China (Mainland)
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