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[ CAS No. 1123-93-9 ] {[proInfo.proName]}

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Chemical Structure| 1123-93-9
Chemical Structure| 1123-93-9
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Walczak, Juliusz Maksymilian ; Iwaszkiewicz-Grzes, Dorota ; Ziomkowska, Michalina , et al. DOI: PubMed ID:

Abstract: The group of 18 new amide derivatives of mycophenolic acid (MPA) and selected heterocyclic amines was synthesised as potential immunosuppressive agents functioning as inosine-5′-monophosphate dehydrogenase (IMPDH) uncompetitive inhibitors. The synthesis of 14 of them employed uronium-type activating system (TBTU/HOBt/DIPEA) while 4 of them concerned phosphonic acid anhydride method (T3P/Py) facilitating amides to be obtained in moderate to excellent yields without the need of phenolic group protection. Most of optimised protocols did not require complicated reaction work-ups, including chromatographic, solvent-consuming methods. The biological activity assay was performed on the T-Jurkat cell line and peripheral mononuclear blood cells (PBMCs) which are both dedicated for antiproliferative activity determination. Each of designed derivatives was characterised by reduced cytotoxicity and benzoxazole analogue (A2) revealed the most promising activity. Subsequently, an observed structure-activity relationship was discussed.

Keywords: Mycophenolic acid ; amide derivatives ; heterocycles ; benzoxazole ; IMPDH inhibition

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Product Details of [ 1123-93-9 ]

CAS No. :1123-93-9 MDL No. :MFCD04115282
Formula : C7H6N2S Boiling Point : -
Linear Structure Formula :- InChI Key :UJZYHMZRXGNDFB-UHFFFAOYSA-N
M.W : 150.20 Pubchem ID :70749
Synonyms :

Calculated chemistry of [ 1123-93-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.02
TPSA : 67.15 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.43
Log Po/w (XLOGP3) : 1.33
Log Po/w (WLOGP) : 1.89
Log Po/w (MLOGP) : 0.85
Log Po/w (SILICOS-IT) : 2.47
Consensus Log Po/w : 1.59

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.28
Solubility : 0.797 mg/ml ; 0.00531 mol/l
Class : Soluble
Log S (Ali) : -2.34
Solubility : 0.684 mg/ml ; 0.00456 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.59
Solubility : 0.384 mg/ml ; 0.00256 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.92

Safety of [ 1123-93-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1123-93-9 ]

* 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.

  • Upstream synthesis route of [ 1123-93-9 ]
  • Downstream synthetic route of [ 1123-93-9 ]

[ 1123-93-9 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 2942-07-6 ]
  • [ 1123-93-9 ]
YieldReaction ConditionsOperation in experiment
52%
Stage #1: With tin(ll) chloride In isopropyl alcohol for 24 h; Heating / reflux
Stage #2: With sodium hydroxide In water; isopropyl alcohol
A mixture OF 5-NITRO-1, 3-benzothiazole (Description 5,1. 9 g, 11 mmol) and tin (II) chloride dihydrate (8.6 g, 38 mmol) in 2-propanol (30 ml) was heated to reflux for 24 h. The cooled reaction mixture was poured onto an ice/water mixture (85 ml) and adjusted to pH7 with sodium hydroxide (s). The mixture was extracted with ethyl acetate (3 X 50 ml) and the combined organic layers were dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography on silica (eluant 1 : 1 hexane: ethyl acetate) to give 1, 3-benzothiazol-5-amine (820 mg, 52 percent). LHNMR (CDCL3) 6 6.85 (1H, dd, J2. 3,8. 6), 7.40 (1H, d, J2. 1), 7.66 (1H, d, J 8.4), 8.90 (1H, s).
2.1 g With tin(II) chloride dihdyrate In ethyl acetateReflux A mixture of 5-nitrobenzo[d]thiazole (3.0 g, 16.7 mmol) and SnCl2*2H2O (19 g, 84.2 mmol) in EtOAc (150 mL) was stirred at reflux overnight. The reaction mixture was basified with Et3N until pH 8 and the precipitate was filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel (EtOAc/DCM = 2:1) to afford the title compound as a yellow solids (2.1 g). 1H NMR (400 MHz, CDCl3): ö 8.92 (s, 1H), 7.69 (d, 1H), 7.41 (d, 1H), 6.86 (dd, 1H), 3.82 (brs, 2H); LCMS: 151 (M+H).
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 3, p. 957 - 971
[2] Catalysis Letters, 2014, vol. 144, # 7, p. 1258 - 1267
[3] Patent: WO2005/28445, 2005, A2, . Location in patent: Page/Page column 28
[4] Yakugaku Zasshi, 1942, vol. 62, p. 47,51; dtsch. Ref. S. 19, 22[5] Chem.Abstr., 1951, p. 609
[6] Helvetica Chimica Acta, 1950, vol. 33, p. 1429,1431
[7] Zhurnal Obshchei Khimii, 1956, vol. 26, p. 3388,3390; engl. Ausg. S. 3773
[8] Zhurnal Obshchei Khimii, 1956, vol. 26, p. 797,800; engl. Ausg. S. 911, 913
[9] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1972, vol. 8, p. 36 - 38[10] Khimiya Geterotsiklicheskikh Soedinenii, 1972, vol. 8, # 1, p. 38 - 40
[11] Patent: US5677321, 1997, A,
[12] Patent: US2006/35897, 2006, A1, . Location in patent: Page/Page column 23
[13] Patent: WO2008/8821, 2008, A2, . Location in patent: Page/Page column 42; 43
[14] Patent: WO2007/48070, 2007, A2, . Location in patent: Page/Page column 112
[15] Phytochemistry, 2012, vol. 74, p. 159 - 165
[16] Patent: WO2013/142266, 2013, A1, . Location in patent: Page/Page column 00506
  • 2
  • [ 2942-07-6 ]
  • [ 1123-93-9 ]
Reference: [1] Patent: US2001/345, 2001, A1,
  • 3
  • [ 98556-09-3 ]
  • [ 1123-93-9 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1972, vol. 8, p. 36 - 38[2] Khimiya Geterotsiklicheskikh Soedinenii, 1972, vol. 8, # 1, p. 38 - 40
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 3, p. 957 - 971
  • 4
  • [ 6283-25-6 ]
  • [ 1123-93-9 ]
Reference: [1] Phytochemistry, 2012, vol. 74, p. 159 - 165
  • 5
  • [ 53666-48-1 ]
  • [ 1123-93-9 ]
Reference: [1] Phytochemistry, 2012, vol. 74, p. 159 - 165
  • 6
  • [ 10403-47-1 ]
  • [ 1123-93-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 3, p. 957 - 971
  • 7
  • [ 58759-63-0 ]
  • [ 1123-93-9 ]
Reference: [1] Helvetica Chimica Acta, 1950, vol. 33, p. 1429,1431
  • 8
  • [ 97-00-7 ]
  • [ 1123-93-9 ]
Reference: [1] Helvetica Chimica Acta, 1950, vol. 33, p. 1429,1431
  • 9
  • [ 1123-93-9 ]
  • [ 769-19-7 ]
YieldReaction ConditionsOperation in experiment
2.3 g With bromine In chloroform at 10 - 20℃; for 1 h; A solution of Br2 (2.3 g, 14.4 mmol) in CHC13 (10 mL) was added dropwise to a solution of benzo[d]thiazol-5-amine (2.1 g, 14.0 mmol) in CHC13 (100 mL) at 10 °C. The mixture was stirred at room temperature for 1 hour. The reaction mixture was basified with saturated aqueous Na2CO3 (100 mL) and extracted with DCM (3x30 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (EtOAc/petroleum ether = 1 :81 :4) to afford the title compound as yellow solids (2.3 g). 1H NMR (300 MHz, CDCl3): ö 9.01 (s, 1H), 7.66 (d, 1H), 6.95 (d, 1H), 4.33 (s, 2H).
Reference: [1] Journal of the Chemical Society, 1965, p. 2248 - 2250
[2] Patent: US2009/118295, 2009, A1, . Location in patent: Page/Page column 23-24
[3] Patent: WO2013/142266, 2013, A1, . Location in patent: Paragraph 00507
  • 10
  • [ 1336-21-6 ]
  • [ 1123-93-9 ]
  • [ 769-19-7 ]
Reference: [1] Patent: US2001/345, 2001, A1,
  • 11
  • [ 1123-93-9 ]
  • [ 58249-57-3 ]
Reference: [1] Journal of Organic Chemistry, 1976, vol. 41, # 8, p. 1328 - 1331
  • 12
  • [ 1123-93-9 ]
  • [ 768-11-6 ]
Reference: [1] Journal of Organic Chemistry, 1976, vol. 41, # 8, p. 1328 - 1331
[2] Patent: US2006/35897, 2006, A1, . Location in patent: Page/Page column 23
[3] Patent: WO2008/8821, 2008, A2, . Location in patent: Page/Page column 42
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