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[ CAS No. 1892-57-5 ] {[proInfo.proName]}

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Chemical Structure| 1892-57-5
Chemical Structure| 1892-57-5
Structure of 1892-57-5 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations      Expand+

Aryal, Pramod ; Bietsch, Jonathan ; Grandhi, Gowri Sankar , et al. DOI:

Abstract: Diarylethenes (DAEs) are an important class ofphotoswitchable compounds that typically undergo reversiblephotochemical conversions between the open and closed cyclizedforms upon treatment with UV light or visible light. In this study,we introduced thioacid functional groups to several photochromicdithienylethene (DTE) derivatives and established a method thatcan be used to prepare these photoswitchable thioacids. Fourthioacid-functionalized diarylethene derivatives were synthesizedthrough the activation of carboxylic acids with N-hydroxysuccini-mide, followed by reactions with sodium hydrosulfide with yields over 90%. These derivatives exhibited reversible photoswitchingand photochromic properties upon treatment with ultraviolet (UV) and visible lights. The thioacid groups on these compounds canact as reaction sites for attaching other desirable functionalities. The photochromic properties of these new derivatives werecharacterized by using ultraviolet?visible (UV?vis) spectroscopy. The photocyclizations of one of the derivatives and its potassiumsalt were also characterized by using nuclear magnetic resonance (NMR) spectroscopy. The anions of the thioacid formed water-soluble photochromic systems, and their applications as colorimetric sensors in agarose hydrogels were demonstrated.

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Adrian O. Dukes ; Pathum M. Weerawarna ; Allison N. Devitt , et al. DOI: PubMed ID:

Abstract: Inhibition of human ornithine aminotransferase interferes with and metabolism in hepatocellular carcinoma, depriving tumors of essential nutrients. A proposed mechanism-based inhibitor containing a bicyclo[3.1.1]heptanol warhead is reported herein. The proposed inactivation mechanism involves a novel α-iminol rearrangement. The synthesis of the proposed inhibitor features an asymmetric intramolecular , utilizing a chiral sulfinamide. This study presents a novel approach toward the synthesis of functionalized bicyclo[3.1.1]heptanes and highlights an underutilized method to access enantiopure exocyclic amines.

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Vlasenko, Yulia A ; To, Avery J ; Fortier, Tess , et al. DOI: PubMed ID:

Abstract: Herein, the successful syntheses of D3- and 13C-N-methyl and D9-tert-butyl Hoechst dyes are presented. This includes the preparation of the labelled D3- and 13C-N-methyl piperazines and D9-tert-butylated hydroxytoluene precursors. The tert-butyl Hoechst dye is known to bind a specific RNA aptamer. Spectroscopic NMR studies of the labelled Hoechst dye-aptamer complexes allowed for the unambiguous assignment of chemical shifts, as well as the dynamics of the bound dye.

Keywords: 13C- ; D- ; Hoechst dye ; NMR spectroscopy

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Giménez-Warren, Javier ; Pe?a, álvaro ; Heredero, Juan , et al. DOI:

Abstract: Ionizable lipids are an essential component of lipid nanoparticles (LNPs) for an efficient mRNA delivery. However, optimizing their chemical structures for high protein expression, efficient endosomal escape, and selective organ targeting remains challenging due to complex structure-activity relationships and multistep synthesis. In this study, we introduce a rapid, high-throughput platform for screening ionizable lipids using a two-step, scalable synthesis involving a one-pot 3-component click-like reaction. This method, herein known as the STAAR approach, standing for Sequential Thiolactone Amine Acrylate Reaction, allowed for the combinatorial synthesis and in vivo screening of 91 novel lipids, followed by a structure-activity study. This led to the development of CP-LC-0729, an ionizable lipid that significantly surpasses the benchmark in protein expression while showing no in vivo toxicity. Additionally, the STAAR lipid platform was further validated by incorporating a one-step strategy to yield a permanently cationic lipid which was tested following a fifth-lipid formulation strategy. The in vivo results showed a highly selective lung delivery with a 32-fold increase in protein expression, outperforming current endogenous targeting strategies. All these findings underscore the potential of lipid CP-LC-0729 and the STAAR lipid platform in advancing the efficiency and specificity of mRNA delivery systems, while also advancing the development of new ionizable lipids.

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Product Details of [ 1892-57-5 ]

CAS No. :1892-57-5 MDL No. :MFCD00044916
Formula : C8H17N3 Boiling Point : -
Linear Structure Formula :N((CH2)3N(CH3)2)CNC2H5 InChI Key :LMDZBCPBFSXMTL-UHFFFAOYSA-N
M.W : 155.24 Pubchem ID :15908
Synonyms :
Chemical Name :N1-((Ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine

Calculated chemistry of [ 1892-57-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.88
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.52
TPSA : 27.96 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.88
Log Po/w (XLOGP3) : 1.87
Log Po/w (WLOGP) : 1.13
Log Po/w (MLOGP) : 0.97
Log Po/w (SILICOS-IT) : 1.72
Consensus Log Po/w : 1.72

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.65
Solubility : 3.47 mg/ml ; 0.0224 mol/l
Class : Very soluble
Log S (Ali) : -2.08
Solubility : 1.29 mg/ml ; 0.00834 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.12
Solubility : 1.18 mg/ml ; 0.00759 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.14

Safety of [ 1892-57-5 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P260-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352+P312-P314-P333+P313-P391-P405-P501 UN#:2922
Hazard Statements:H302-H311-H314-H373-H410 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1892-57-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1892-57-5 ]

[ 1892-57-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 2886-33-1 ]
  • [ 88950-64-5 ]
  • [ 1892-57-5 ]
  • [ 1415763-45-9 ]
YieldReaction ConditionsOperation in experiment
94% With hydrogenchloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In dichloromethane; Step 1. Synthesis of 1-[(tert-butoxycarbonyl)amino]cyclopropanecarbonyl-L-aspartic acid dibenzyl ester To a solution of 1-(tert-butoxycarbonyl)aminocyclopropanecarboxylic acid (257 mg, 1.28 mmol), L-aspartic acid dibenzyl ester tosylate (806 mg, 1.66 mmol), WSC hydrochloride (367 mg, 1.92 mmol), and 1-hydroxybenzotriazole (291 mg, 1.92 mmol) in dichloromethane (4.0 ml) was added N,N-diisopropylethylamine (1.30 mL, 7.66 mmol), and the mixture was stirred at room temperature for 7 hours. 1N Hydrochloric acid was added to the reaction mixture, the mixture was extracted 3 times with dichloromethane, and the obtained dichloromethane layer was washed with saturated brine. After drying over anhydrous magnesium sulfate, the desiccant was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (598 mg, 1.20 mmol, 94%). 1H NMR (400 MHz, CDCl3) delta 7.41-7.23 (10H, m), 5.14 (2H, s), 5.11-4.96 (2H, m), 4.93-4.82 (1H, m), 3.08 (1H, dd, J=17.1, 4.3 Hz), 2.92 (1H, dd, J=17.1, 3.8 Hz), 1.60-1.49 (2H, m), 1.44 (9H, s), 1.09-0.96 (2H, m). MS (ESI) m/z 497 (M+H)+
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