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[ CAS No. 107-96-0 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
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Chemical Structure| 107-96-0
Chemical Structure| 107-96-0
Structure of 107-96-0 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

Chen, Jing ; Ji, Peng ; Gnawali, Giri , et al. DOI: PubMed ID:

Abstract: The current targeting drug delivery mainly relies on cancer cell surface receptors. However, in many cases, binding affinities between protein receptors and homing ligands is relatively low and the expression level between cancer and normal cells is not significant. Distinct from conventional targeting strategies, we have developed a general cancer targeting platform by building artificial receptor on cancer cell surface via a chemical remodeling of cell surface glycans. A new tetrazine (Tz) functionalized chemical receptor has been designed and efficiently installed on cancer cell surface as "overexpressed" biomarker through a metabolic glycan engineering. Different from the reported bioconjugation for drug targeting, the tetrazine labeled cancer cells not only locally activate TCO-caged prodrugs but also release active drugs via the unique bioorthogonal Tz-TCO click-release reaction. The studies have demonstrated that the new drug targeting strategy enables local activation of prodrug, which ultimately leads to effective and safe cancer therapy.

Keywords: Artificial receptor ; Click and release ; Local activation ; Protein degradation

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Product Details of [ 107-96-0 ]

CAS No. :107-96-0 MDL No. :MFCD00004897
Formula : C3H6O2S Boiling Point : No data available
Linear Structure Formula :- InChI Key :DKIDEFUBRARXTE-UHFFFAOYSA-N
M.W : 106.14 Pubchem ID :6514
Synonyms :

Calculated chemistry of [ 107-96-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 26.24
TPSA : 76.1 ?2

Pharmacokinetics

GI absorption : High
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) : -6.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.82
Log Po/w (XLOGP3) : 0.43
Log Po/w (WLOGP) : 0.39
Log Po/w (MLOGP) : 0.03
Log Po/w (SILICOS-IT) : 0.13
Consensus Log Po/w : 0.36

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -0.64
Solubility : 24.5 mg/ml ; 0.231 mol/l
Class : Very soluble
Log S (Ali) : -1.6
Solubility : 2.69 mg/ml ; 0.0254 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.1
Solubility : 83.3 mg/ml ; 0.785 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.28

Safety of [ 107-96-0 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P234-P261-P264-P270-P271-P273-P280-P301+P310+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P363-P390-P405-P406-P501 UN#:2922
Hazard Statements:H290-H301-H314-H332-H401 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 107-96-0 ]

* 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 [ 107-96-0 ]

[ 107-96-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 38222-83-2 ]
  • [ 77758-76-0 ]
  • [ 107-96-0 ]
  • 3-pentafluoroethylthiopropionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; REFERENCE EXAMPLE 4 2.0 ml of methylene chloride, 0.05 ml (0.58 mmol) of 3-mercaptopropionic acid and 120 mg (0.59 mmol) of <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> were charged in a flask, and 261 mg (0.55 mmol) of pentafluoroethylphenyliodonium trifluoromethanesulfonate was added thereto in small portions while stirring at room temperature, followed by stirring the mixture at room temperature for 20 minutes. The resulting white precipitate was filtered, subjected to column chromatography of a small amount of silica gel and, after eluding iodobenzene with hexane, the desired product was eluted with diethyl ether. Diethyl ether was distilled off from the elude to obtain 3-pentafluoroethylthiopropionic acid as a colorless liquid. A sample of the product was purified by gas chromatography. Yield, 83percent. 19 F-NMR (CCl3 F internal standard in CDCl3): -84.00 ppm (t, JCF3,CF2 =3.5 Hz, CF3, 3F), -92.82 ppm (q, JCF3,CF2 =3.5 Hz, CF2, 2F) 1 H-NMR (in CDCl3): 2.79 ppm (t, J=7.0 Hz, CH2 SC2 F5, 2H), 3.15 ppm (t, J=7.0 Hz, --CH2 CO--, 2H), 10.6 ppm (br.s, CO2 H, 1H). IR (neat): 3050 (broad absorption), 2670, 2480, 1720, 1430, 1330, 1215, 1100, 970, 920, 810, 750, 650, 625, 585, 555 cm-1. MS: 224 (M+), 179, 105, 87, 69, 63, 59, 45. Elementary Analysis: Found: C, 26.83; H, 2.31percent. Calc'd: C, 26.79; H, 2.25percent.
  • 2
  • [ 2645-22-9 ]
  • [ 107-96-0 ]
  • [ 192331-71-8 ]
  • 3
  • [ 391-12-8 ]
  • [ 95-51-2 ]
  • [ 107-96-0 ]
  • [ 1373763-20-2 ]
YieldReaction ConditionsOperation in experiment
92% With 1-methylimidazolium tetrafluoroborate; at 140℃; for 0.05h;Microwave irradiation; Ionic liquid; Pyrex glass vial containing an equimolar mixture (5 mmol) of appropriate indole-2,3-dione (1) and substituted aniline (2) and thioacids (3a/b) adsorbed on 1-methylimidazolium tetrafluoroborate ([MIM]+BF4-) (1 gm) was placed in a screw capped Teflon vessel. Microwave was applied for 5 min at 140 °C. After the completion of reaction (TLC analysis), recyclable ionic liquid was separated by filtration after eluting the product with ethanol under reduced pressure and the residue washed with methanol gave a pure product in high yield (Table 1). All synthesized compounds were characterized by spectral analysis and data summarized in Table 4.
  • 4
  • [ 64987-85-5 ]
  • [ 107-96-0 ]
  • MPr-SMCC [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With N-ethyl-N,N-diisopropylamine; The drug-linker SMCC-MDC was prepared in the following reactions: (1) 3-mercaptopropanoic acid (MPr) was reacted with N-succinimidyl 4-(maleimidomethyl)cyclohexane-1-carboxylate (SMCC) in the presence of N,N-diisopropylethylamine (DIEA), giving the MPr-SMCC at a yield of over 95percent;
95% With N-ethyl-N,N-diisopropylamine; The drug-linker SMCC-MDC was prepared in the following reactions: (1) 3-mercaptopropanoic acid (MPr) was reacted with N-succinimidyl 4-(maleimidomethyl)cyclohexane-1-carboxylate (SMCC) in the presence of N,N-diisopropylethylamine (DIEA), giving the MPr-SMCC at a yield of over 95percent;
95% With N-ethyl-N,N-diisopropylamine; The drug-linker SMCC-MDC was prepared in the following reactions: (1) 3-mercaptopropanoic acid (MPr) was reacted with N-succinimidyl 4-(maleimidomethyl)cyclohexane-1-carboxylate (SMCC) in the presence of N,N-diisopropylethylamine (DIEA), giving the MPr-SMCC at a yield of over 95percent;
> 95% With N-ethyl-N,N-diisopropylamine; The drug-linker SMCC-MDC was prepared in the following reactions: (1) 3-mercaptopropanoic acid (MPr) was reacted with N-succinimidyl 4-(maleimidomethyl)cyclohexane-1-carboxylate (SMCC) in the presence of DIEA, giving the MPr-SMCC at a yield of over 95percent; Secondly, condensation of N-Me-L-Ala-MDC, which was prepared by deprotection of Fmoc-N-Me-Ala-MDC under a base piperidine in CH3CN, with MPr-SMCC under a coupling reagent EDC, giving the desired coupled product SMCC-MDC in 60-70percent yield over two steps. Antibody Bat0206 (Abu) was diluted to 2.5 mg/mL in solution A (50 mM potassium phosphate, 50 mM NaCl, and 2 mM EDTA, pH 6.5). SMCC-MDC was added to give a ratio of SMCC-MDC to antibody of 7:1 mole equivalent. Then DMA was added to 15percent (v/v) to the reaction and reaction was mixed by stirring for 4 h at ambient temperature. D-Lmcc-Bat0206 conjugate was purified from excess unreacted or hydrolyzed reagent and excess SMCC-MDC using a G25 gel filtration column equilibrated in pH 7.4 phosphate buffer (aqueous). The conjugate was then dialyzed overnight into pH 7.4 phosphate buffer (aqueous) and then filtered through a 0.22 mum filter for final storage. The number of SMCC-MDC molecule per Abu molecule in the final conjugate was measured by determining absorbance of the conjugate at 252 and 280 nm and using known extinction coefficients for SMCC-MDC and antibody at these two wavelengths. A ratio of maytansinoid compound to antibody of 3.5:1.0 was normally obtained.
95% With triethylamine; In dichloromethane; at 20℃; for 2h; In the solution of SMCC (3 g) in anhydrous CH2Cl2 (80 ml), mercaptoacetic acid (0.937 ml) and triethylamine (1.428 ml) wereadded. The mixture was stirred for 2 h at room temperature. After evaporation of the solvent under vacuum, the solid was purified by column chromatography (CH2Cl2:Methanol = 20:1) to yield compound 2(3.76 g, 95percent). The structure was identified by ESI-QTOF-MS, 1H and 13C NMR. (M + H)+ = 441.1591; (M + Na)+ = 463.1132. 1H NMR(400 MHz, DMSO-d6): delta 12.33 (s, 1H), 4.02 (1H,dd, J = 8.9, 3.8 Hz), 3.25(d,2H, J = 7.0 Hz), 3.22?3.13 (m, 1H), 2.94 (dd,1H,J = 13.5, 6.7 Hz),2.86 (dd,1H,J = 13.7, 6.7 Hz), 2.8 (s,3H), 2.69 (t,1H,J = 12.0 Hz), 2.62?2.44 (m, 4H), 2.00 (d,2H,J = 11.1 Hz), 1.69 (d,3H,J = 13.3 Hz), 1.48?1.27 (m, 2H), 1.05 (dd,2H,J = 23.6, 11.0 Hz). 13C NMR (100 MHz,DMSO-d6): delta 177.0, 175.3, 172.8, 170.8, 170.2, 43.7, 35.6, 34.9, 34.0, 28.5,27.8, 26.8, 25.4.

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