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[ CAS No. 294-90-6 ] {[proInfo.proName]}

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Chemical Structure| 294-90-6
Chemical Structure| 294-90-6
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Product Citations

Product Citations      Expand+

Tang, Jian-Hong ; Luo, Minrui ; Tsao, Wilhelmina , et al. DOI: PubMed ID:

Abstract: Glycoconjugates forming from the conjugation of carbohydrates to other biomolecules, such as proteins, lipids, or other carbohydrates, are essential components of mammalian cells and are involved in numerous biological processes. Due to the capability of sugars to form multiple hydrogen bonds, many synthetic glycoconjugates are desirable biocompatible platforms for imaging, diagnostics, drugs, and supramolecular self-assemblies. Herein, we present a multimeric galactose functionalized paramagnetic gadolinium (Gd(III)) chelate that displays spontaneous dynamic aggregation in aqueous conditions. The dynamic aggregation of the Gd(III) complex was shown by the concentration-dependent magnetic resonance (MR) relaxation measurements, nuclear magnetic resonance dispersion (NMRD) analysis, and dynamic light scattering (DLS). Notably, these data showed a nonlinear relationship between magnetic resonance relaxation rate and concentrations (0.03?1.35 mM), and a large DLS hydrodynamic radius was observed in the high-concentration solutions. MR phantom images were acquired to visualize real-time dynamic aggregation behaviors in aqueous solutions. The in situ visualization of the dynamic self-assembling process of multivalent glycoconjugates has rarely been reported.

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Li, Bowen ; Manan, Rajith Singh ; Liang, Shun-Qing , et al. DOI: PubMed ID:

Abstract: The expanding applications of nonviral genomic medicines in the lung remain restricted by delivery challenges. Here, leveraging a high-throughput platform, we synthesize and screen a combinatorial library of biodegradable ionizable lipids to build inhalable delivery vehicles for mRNA and CRISPR-Cas9 gene editors. Lead lipid nanoparticles are amenable for repeated intratracheal dosing and could achieve efficient gene editing in lung epithelium, providing avenues for gene therapy of congenital lung diseases.

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Product Details of [ 294-90-6 ]

CAS No. :294-90-6 MDL No. :MFCD00066281
Formula : C8H20N4 Boiling Point : -
Linear Structure Formula :- InChI Key :QBPPRVHXOZRESW-UHFFFAOYSA-N
M.W : 172.27 Pubchem ID :64963
Synonyms :
Chemical Name :1,4,7,10-Tetraazacyclododecane

Calculated chemistry of [ 294-90-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 4.0
Num. H-bond donors : 4.0
Molar Refractivity : 65.32
TPSA : 48.12 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -9.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.81
Log Po/w (XLOGP3) : -2.36
Log Po/w (WLOGP) : -3.16
Log Po/w (MLOGP) : -0.83
Log Po/w (SILICOS-IT) : 0.31
Consensus Log Po/w : -0.85

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.58
Solubility : 653.0 mg/ml ; 3.79 mol/l
Class : Highly soluble
Log S (Ali) : 1.89
Solubility : 13300.0 mg/ml ; 77.1 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -2.31
Solubility : 0.85 mg/ml ; 0.00493 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.01

Safety of [ 294-90-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P273-P260-P270-P264-P280-P391-P362+P364-P303+P361+P353-P301+P330+P331-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405 UN#:3259
Hazard Statements:H302+H312-H314-H410 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 294-90-6 ]

* 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 [ 294-90-6 ]

[ 294-90-6 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 16644-30-7 ]
  • [ 294-90-6 ]
  • [ 690253-70-4 ]
YieldReaction ConditionsOperation in experiment
~ 12% With triethylamine; In tetrahydrofuran; A compound having the structure shown as the final product in the scheme detailed in FIG. 4 was synthesized and characterized. Reaction step (1) (shown in isolation in FIG. 6) proceeds well and the product was characterized by 1H NMR spectroscopy (peak obtained at MW=214). This product was readily purified by recrystallization from hot n-hexane. The yield of this reaction in our hands was not established. The literature value is 89% isolated yield. L. D. Taylor and R. B. Davis, J. Org. Chem. 1963, 28, 1713. [0074] Reaction step (2) (shown in isolation in FIG. 7) also proceeded and the crude product was purified by recrystallization from ethanol/tetrahydrofuran. Small, square-shaped orange crystals were obtained over a period of two days in ca. 12% yield. Analysis of these crystals via 1H NMR spectroscopy suggests that their crystal structure may contain tetrahydrofuran (see FIG. 8). Mass spectroscopy yielded an m/z peak at 352. Further addition of tetrahydrofuran to the ethanol mixture yielded a second crop of similar crystals. However, this second crop was coated in orange-colored viscous oil, characteristic of material that had come out of solution too quickly. This material is to be further recrystallized to improve product yield. [0075] Reaction step (3) (shown in isolation in FIG. 9) was carried out under reflux (approximately 80 C.) proceeded well and yielded a solid product as expected. Previous attempts to synthesize this compound have yielded viscous oil. Purification of the product from reaction (2) appears to lead to a purer product from reaction (3) as we obtained a solid instead of an oil. This product was analyzed by 1H NMR and by ES mass spectral analysis: FW ca. 506, [M]+504 (100%). [0076] Reaction step (4) (shown in isolation in FIG. 10) was conducted overnight at pH=10-11. However, the pH dropped to a value of 9 after 24 h. Thus, the pH was again raised to a value of ca. 10 and allowed to react for a further 24 h, during which time the reaction mixture maintained its pH value of ca. 10. It appears that at least 48 hours are necessary for the reaction to go to completion as indicated by the lack of further pH change. ES mass spectral analysis indicated a prominent peak at 701 (expected mass of the ligand+Na+). [0077] Reaction step 5 (i.e., the final reaction step shown in FIG. 4) involves the insertion of the metal to the macrocycle. The sample was run through a Chelex 100 column after first neutralizing the reaction mixture to pH=7. However, upon eluting with water, only pale yellow oil was obtained. This did not display the characteristic absorbances of ca. 510 and 550 nm upon exposure to UV-light irradiation. In addition, it was observed that a band of purple-colored material was trapped at the top of the Chelex column. Various solvents were used to try to pass this band through the column, and ethanol and chloroform each were found to be effective to elute the product. This purple-colored material displayed characteristic color changes expected for the final product. UV irradiation (described in the following example) produced a product with absorbances at ca. 510 and 550 nm. Irradiation with white light eliminates these absorbance peaks. Mass spec for the product from step 5 yielded a peak at 835 and also peak at 678 (representing either free ligand or artifactual dissociation of product during electrospray).
  • 2
  • [ 3913-23-3 ]
  • [ 294-90-6 ]
  • N-(2-methoxy-5-nitrobenzyl)-1,4,7,10-tetraazacyclododecane [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% In chloroform; EXAMPLE E Preparation of N-(2-methoxy-5-nitrobenzyl)-1,4,7,10-tetraazacyclododecane. To a stirred chloroform solution (20 ml) containing 2.9 g of 1,4,7,10-tetraazacyclododecane (16.8 mmole) was added a chloroform solution (20 ml) containing 2.1 g of <strong>[3913-23-3]2-methoxy-5-nitrobenzyl bromide</strong> (8.5 mmole) in one portion. After stirring at room temperature for three hours the reaction mixture was filtered and the filtrate concentrated (in vacuo) to give a residue which was chromatographed (silica, Solvent System 3). The monoalkylated product was isolated in 79 percent yield (MP=154-156 C.), and characterized by: 13 C NMR (CDCl3) 162.47, 140.63, 127.92, 125.49, 124.53, 109.91, 55.88, 53.25, 50.90, 47.18, 45.45, 45.29.
  • 3
  • [ 2895-21-8 ]
  • [ 294-90-6 ]
  • [ 1105681-51-3 ]
  • 4
  • [ 3792-04-9 ]
  • [ 294-90-6 ]
  • [ 1211942-04-9 ]
  • 5
  • [ 3792-04-9 ]
  • [ 294-90-6 ]
  • [ 1269772-31-7 ]
  • 6
  • [ 3792-04-9 ]
  • [ 294-90-6 ]
  • [ 1269772-29-3 ]
  • 7
  • [ 57280-22-5 ]
  • [ 3926-62-3 ]
  • [ 294-90-6 ]
  • 10-(2,3-dihydroxy-1-hydroxymethylpropyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triacetate gadolinium [ No CAS ]
YieldReaction ConditionsOperation in experiment
160 kg of cyclen (1 ,4,7, 10-tetraazacyclododecane), 154 kg of 4,4-dimethyl-3,5,8- trioxabicyclo[5,1 ,0]octane and 34.7 kg of lithium chloride are initially charged in 325 kg of isopropanol and heated under reflux for 1320 minutes.1250 I of water are added, and the mixture is distilled until an internal temperature of 78C is reached. The mixture is then made up with 805 I of water, and 375 kg of sodium monochloroacetate are added at 35C, followed by 120 kg of 50% strength aqueous sodium hydroxide solution. The mixture is heated to an internal temperature of 65C, and a further 85 kg of 50% strength aqueous sodium hydroxide solution are added. If the pH drops below 12, it is re-adjusted with 10 kg of 50% strength aqueous sodium hydroxide solution (step-wise). The mixture is stirred at an internaltemperature of 65C for 90 minutes. After cooling to 50C, 240 kg of 36% aqueous hydrochloric acid are added such that the pH is now 3.1 - 4.9 (if appropriate, additional hydrochloric acid has to be added; it is important that the target pH is reached). At a jacket temperature of 95C and under reduced pressure, solvent (isopropanol/water mixture) is then distilled off to a total amount of 1200 kg.At 40C, 2554 kg of methanol are added and the pH is adjusted to 1.4 or less (1 .1 - 1 .3, optimum 1 .2) using 282 kg of 36% aqueous hydrochloric acid. The mixture is stirred at 40C for 35 minutes. The mixture is then cooled to 20C and theprecipitated sodium chloride (NaCI) is separated off using a centrifuge or a pressure nutsche filter (the filter cake is washed with methanol since the product is in solution). 996 (this is still being examined) I of water are added, and the methanol issubstantially distilled off at a jacket temperature of 90C (250 mbar), with water, the mixture is concentrated to a mass of 966 kg, and a further 1200 I of water are then added. 155 kg of gadolinium oxide are added to this solution, and the mixture is heated at 95C for 120 minutes. The mixture is allowed to cool to 50C and adjusted to pH 7.1 - 7.4 using lithium hydroxide monohydrate (this requires about 85 kg of lithium hydroxide monohydrate). At a jacket temperature of 120C and under reduced pressure, 895 kg of water are then distilled off. The mixture is allowed to cool to 73C, 5286 kg of alcohol (MEK = methyl ethyl ketone denaturized) are added and the water content is checked using the Karl-Fischer method. The water content is adjusted to 8.5%. (If the value is less than 7.0, an appropriately calculated amount of water is added. If the value is greater than 9.5%, an appropriate amount of ethanol is added. For the process, it is important that the value is in the range from 7.0 to 9.5). The mixture is then heated under reflux (78C) for 60 minutes. Eventually,spontaneous crystallization occurs. The mixture is stirred at a jacket temperature of 100C for 480 minutes and then allowed to cool to 20C.The product is isolated using a centrifuge or pressure nutsche, the filter cake twice being washed with ethanol. In a paddle drier, the crude product is dried at a jacket temperature of 58C for 90 minutes under reduced pressure (until a pressure of < 62 mbar and a temperature of > 46C are reached) or washed with ethanol three times and dried at < 34C. The product is then dried at an internal temperature of 48C for 60 minutes. The crude product is cooled to 20C and filled into containers. This gives 540 kg of a colourless crystalline powder (yield > 96%).
  • 8
  • [ 4876-10-2 ]
  • [ 294-90-6 ]
  • 4-((1,4,7,10-tetraazacyclododecan-1-yl)methyl)quinoline-2(1H)-one [ No CAS ]
  • 9
  • [ 4876-10-2 ]
  • [ 294-90-6 ]
  • [Zn(4-((1,4,7,10-tetraazacyclododecan-1-yl)methyl)quinoline-2(1H)-one)]Cl2 [ No CAS ]
  • 10
  • [ 946-99-6 ]
  • [ 294-90-6 ]
  • 1,4,7,10-tetrazazcyclododecane-N,N′,N′′,N′′′-tetramethylenecinnamic acid hydrochloride [ No CAS ]
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[ 294-90-6 ]

Chemical Structure| 10045-25-7

A789089[ 10045-25-7 ]

1,4,7,10-Tetraazacyclododecane tetrahydrochloride

Reason: Free-Salt

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