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[ CAS No. 6341-92-0 ] {[proInfo.proName]}

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Product Citations

Product Citations

Prinsloo, Izak F. ; Petzer, Jacobus P. ; Cloete, Theunis T. , et al. DOI: PubMed ID:

Abstract: The small mol., isatin, is a well-known reversible inhibitor of the monoamine oxidase (MAO) enzymes with IC50 values of 12.3 and 4.86μM for MAO-A and MAO-B, resp. While the interaction of isatin with MAO-B has been characterized, only a few studies have explored structure-activity relationships (SARs) of MAO inhibition by isatin analogs. The current study therefore evaluated a series of 14 isatin analogs as in vitro inhibitors of human MAO-A and MAO-B. The results indicated good potency MAO inhibition for some isatin analogs with five compounds exhibiting IC50 < 1μM. 4-Chloroisatin (1b) and 5-bromoisatin (1f) were the most potent inhibitors with IC50 values of 0.812 and 0.125μM for MAO-A and MAO-B, resp. These compounds were also found to be competitive inhibitors of MAO-A and MAO-B with Ki values of 0.311 and 0.033μM, resp. Among the SARs, it was interesting to note that C5-substitution was particularly beneficial for MAO-B inhibition. MAO inhibitors are established drugs for the treatment of neuropsychiatric and neurodegenerative disorders, while potential new roles in prostate cancer and cardiovascular disease are being investigated.

Keywords: competitive ; inhibition ; isatin ; monoamine oxidase ; structure-activity relationship

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Product Details of [ 6341-92-0 ]

CAS No. :6341-92-0 MDL No. :MFCD00086347
Formula : C8H4ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :RVXLBLSGEPQBIO-UHFFFAOYSA-N
M.W : 181.58 Pubchem ID :241331
Synonyms :

Calculated chemistry of [ 6341-92-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.17
TPSA : 46.17 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) : -6.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.01
Log Po/w (XLOGP3) : 1.27
Log Po/w (WLOGP) : 0.9
Log Po/w (MLOGP) : 0.75
Log Po/w (SILICOS-IT) : 2.15
Consensus Log Po/w : 1.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.14
Solubility : 1.33 mg/ml ; 0.00731 mol/l
Class : Soluble
Log S (Ali) : -1.84
Solubility : 2.63 mg/ml ; 0.0145 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.39
Solubility : 0.0735 mg/ml ; 0.000405 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.48

Safety of [ 6341-92-0 ]

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

Application In Synthesis of [ 6341-92-0 ]

* 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.

  • Upstream synthesis route of [ 6341-92-0 ]
  • Downstream synthetic route of [ 6341-92-0 ]

[ 6341-92-0 ] Synthesis Path-Upstream   1~31

  • 1
  • [ 215959-30-1 ]
  • [ 6341-92-0 ]
YieldReaction ConditionsOperation in experiment
88% With water In methanol for 19 h; Heating / reflux Step 2:
6-Chloroisatin
3,3-Dibromo-6-chloro-1,3-dihydro-indol-2-one (21.34 g, 59.7 mmol) was suspended in a 4:1 (v:v) mixture of MeOH (172 mL): water (43 mL) and heated at reflux for 19 hr.
The reaction was cooled in an ice bath and filtered.
The red solid was washed once with cold CH3OH and dried to give the title compound as a red solid (10.49 g, 88percent yield). NMR (400 MHz, DMSO-d6): consistent. MS: (API-ES+) m/z 182/184 [M+H], 1 chlorine pattern observed.
Reference: [1] Patent: US2005/250798, 2005, A1, . Location in patent: Page/Page column 26
[2] Tetrahedron Letters, 1998, vol. 39, # 42, p. 7679 - 7682
[3] Tetrahedron Letters, 2002, vol. 43, # 26, p. 4671 - 4673
  • 2
  • [ 52537-00-5 ]
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YieldReaction ConditionsOperation in experiment
79% With iodine pentoxide In dimethyl sulfoxide at 80℃; General procedure: Indoles 1 (0.5 mmol), DMSO (3mL) and I2O5 (1 mmol) were added into a flask and vigorously stirred at 80oC under air. The reaction was stopped until indoles were completely consumed as monitored by TLC analysis. After the completion of reaction, saturated Na2S2O3 solution (20 mL) was added to the mixture. The mixture was extracted with EtOAc (3×20 mL) and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator. Then, the crude product was purified by column chromatography on silica gel using ethyl acetate and petroleum ether as the eluent to give the products 2.
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 18, p. 1747 - 1750
  • 3
  • [ 302-17-0 ]
  • [ 108-42-9 ]
  • [ 6341-92-0 ]
YieldReaction ConditionsOperation in experiment
28.6% With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate In water at 90℃; for 0.0833333 h; General procedure: To a solution of 120mL water, chloral hydrate (8.93g, 0.054mol), anhydrous sodium sulfate (130g, 0.40mol), aniline or substituted aniline 5 (0.05mol), hydroxylammonium chloride (10.98g, 0.158mol) and concentrated hydrochloric acid (43mL) were added respectively. Subsequently, the resulting suspension was heated to 90°C for 5min and cooled to room temperature. After filtration and washing with water (2×20mL), the crude material was obtained. The crude was added in batches to a 250mL, three mouth flask filled with concentrated sulfuric acid (32.6mL) at the temperature of 65°C and then heated up to 80°C for 20min. The reaction solution was cooled to room temperature and poured onto 500g of ice water and stirred vigorously for 4h. Intermediates 6a–i were isolated by filtration, washing with water, and recrystallization from ethanol with yields from 25.7percent to 73.2percent.
Reference: [1] Chinese Chemical Letters, 2013, vol. 24, # 10, p. 929 - 933
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 20, p. 5630 - 5633
  • 4
  • [ 56341-37-8 ]
  • [ 6341-92-0 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 12, p. 1575 - 1580
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 1, p. 423 - 426
[3] Tetrahedron Letters, 2002, vol. 43, # 26, p. 4671 - 4673
[4] Tetrahedron Letters, 1998, vol. 39, # 42, p. 7679 - 7682
  • 5
  • [ 17122-55-3 ]
  • [ 6341-92-0 ]
YieldReaction ConditionsOperation in experiment
2.91 g at 50 - 65℃; for 1.33333 h; General procedure: 4.2 General procedure for the synthesis of 5 and 10a–g: (a) A 500 ml, three-necked, round-bottomed flask fitted with a condenser and a thermometer was charged with chloral hydrate (16.50 g, 0.1 mol) and 220 ml of water. Then anhydrous sodium sulfate (15.00 g), aniline derivative (0.1 mol), HCl solution (5.2 percent, 70 ml), and hydroxylamine hydrochloride (20.81 g, 0.3 mol, in 95 ml of water) were added in successively. After being heated to reflux for 1 h, the reaction mixture was cooled to room temperature. The intermediate compound (anilide derivative) was collected by filtration and dried, which was used for next step without further purification. (b) A 100 ml, three-necked, round-bottomed flask fitted with a thermometer was charged with concentrated sulfuric acid (10 equiv). After heating to 50 °C with stirring, the dried product (1 equiv) from the above step was added in over a period of 20 min. The resulting solution was heated to 65 °C and kept for 1 h and then cooled down to room temperature with an ice bath. The precipitate was filtered out and dried to get the target compounds. The dried product from the above step (15.4 g, 0.095 mol) was added into concentrated sulfuric acid (50 ml) in a period of 20 min at 50 °C. Then the resulted mixture was heated to 65 °C and kept for 1 h. The mixture was poured into ice water. The precipitate in the mixture was filtered out and dried.
Reference: [1] European Journal of Pharmacology, 2007, vol. 556, # 1-3, p. 200 - 206
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7349 - 7353
[3] Tetrahedron, 2014, vol. 70, # 4, p. 906 - 913
[4] Medicinal Chemistry Research, 2014, vol. 23, # 5, p. 2161 - 2168
[5] Heterocycles, 2014, vol. 89, # 8, p. 1923 - 1932
[6] Organic and Biomolecular Chemistry, 2015, vol. 13, # 22, p. 6371 - 6379
  • 6
  • [ 17122-55-3 ]
  • [ 6341-92-0 ]
  • [ 6344-05-4 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry, 1990, vol. 29, # 6, p. 578 - 581
[2] Synthetic Communications, 2010, vol. 40, # 21, p. 3125 - 3134
[3] Journal of Medicinal Chemistry, 1992, vol. 35, # 11, p. 2085 - 2094
[4] Journal of Medicinal Chemistry, 2004, vol. 47, # 4, p. 935 - 946
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 2, p. 494 - 499
[6] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 4, p. 764 - 769
  • 7
  • [ 6344-05-4 ]
  • [ 108-42-9 ]
  • [ 6341-92-0 ]
Reference: [1] Patent: US4112098, 1978, A,
  • 8
  • [ 1189051-98-6 ]
  • [ 6341-92-0 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 36, p. 7357 - 7363
  • 9
  • [ 108-42-9 ]
  • [ 6341-92-0 ]
Reference: [1] European Journal of Pharmacology, 2007, vol. 556, # 1-3, p. 200 - 206
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 2, p. 494 - 499
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 4, p. 935 - 946
[4] Journal of Medicinal Chemistry, 1992, vol. 35, # 11, p. 2085 - 2094
[5] Helvetica Chimica Acta, 1919, vol. 2, p. 239
[6] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7349 - 7353
[7] Tetrahedron, 2014, vol. 70, # 4, p. 906 - 913
[8] Medicinal Chemistry Research, 2014, vol. 23, # 5, p. 2161 - 2168
[9] Heterocycles, 2014, vol. 89, # 8, p. 1923 - 1932
[10] Organic and Biomolecular Chemistry, 2015, vol. 13, # 22, p. 6371 - 6379
  • 10
  • [ 302-17-0 ]
  • [ 108-42-9 ]
  • [ 6341-92-0 ]
  • [ 6344-05-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 1, p. 1 - 10
  • 11
  • [ 108-42-9 ]
  • [ 6341-92-0 ]
  • [ 6344-05-4 ]
Reference: [1] Patent: US6576656, 2003, B1,
  • 12
  • [ 98-86-2 ]
  • [ 6341-92-0 ]
  • [ 5439-80-5 ]
Reference: [1] Patent: US5627193, 1997, A,
  • 13
  • [ 10565-16-9 ]
  • [ 6341-92-0 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 42, p. 7679 - 7682
  • 14
  • [ 89-61-2 ]
  • [ 6341-92-0 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 42, p. 7679 - 7682
  • 15
  • [ 6828-35-9 ]
  • [ 6341-92-0 ]
Reference: [1] European Journal of Organic Chemistry, 2016, vol. 2016, # 10, p. 1881 - 1885
  • 16
  • [ 141-85-5 ]
  • [ 6341-92-0 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry, 1990, vol. 29, # 6, p. 578 - 581
  • 17
  • [ 1261152-95-7 ]
  • [ 6341-92-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7349 - 7353
  • 18
  • [ 98591-63-0 ]
  • [ 6341-92-0 ]
Reference: [1] Journal of the Chemical Society, 1958, p. 614,619
  • 19
  • [ 17422-33-2 ]
  • [ 6341-92-0 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 516 - 530
  • 20
  • [ 79-37-8 ]
  • [ 141-85-5 ]
  • [ 6341-92-0 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 647
  • 21
  • [ 98591-63-0 ]
  • [ 7664-93-9 ]
  • [ 7732-18-5 ]
  • [ 6341-92-0 ]
Reference: [1] Journal of the Chemical Society, 1958, p. 614,619
  • 22
  • [ 17122-55-3 ]
  • [ 6341-92-0 ]
  • [ 6344-05-4 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry, 1990, vol. 29, # 6, p. 578 - 581
[2] Synthetic Communications, 2010, vol. 40, # 21, p. 3125 - 3134
[3] Journal of Medicinal Chemistry, 1992, vol. 35, # 11, p. 2085 - 2094
[4] Journal of Medicinal Chemistry, 2004, vol. 47, # 4, p. 935 - 946
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 2, p. 494 - 499
[6] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 4, p. 764 - 769
  • 23
  • [ 302-17-0 ]
  • [ 108-42-9 ]
  • [ 6341-92-0 ]
  • [ 6344-05-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 1, p. 1 - 10
  • 24
  • [ 108-42-9 ]
  • [ 6341-92-0 ]
  • [ 6344-05-4 ]
Reference: [1] Patent: US6576656, 2003, B1,
  • 25
  • [ 6341-92-0 ]
  • [ 6958-39-0 ]
Reference: [1] Journal of Organic Chemistry, 1952, vol. 17, p. 149,153
  • 26
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  • [ 1677-48-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 19, p. 5536 - 5549
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 2697,2700
[3] Journal of Organic Chemistry, 1952, vol. 17, p. 149,153
  • 27
  • [ 6341-92-0 ]
  • [ 89-77-0 ]
Reference: [1] Journal of the American Chemical Society, 1956, vol. 78, p. 1251,1254
  • 28
  • [ 67-56-1 ]
  • [ 6341-92-0 ]
  • [ 5900-58-3 ]
  • [ 89-77-0 ]
Reference: [1] Angewandte Chemie, 1981, vol. 93, # 10, p. 914 - 915
  • 29
  • [ 67-56-1 ]
  • [ 6341-92-0 ]
  • [ 5900-58-3 ]
  • [ 89-77-0 ]
Reference: [1] Angewandte Chemie, 1981, vol. 93, # 10, p. 914 - 915
  • 30
  • [ 6341-92-0 ]
  • [ 56341-37-8 ]
YieldReaction ConditionsOperation in experiment
88% With titanium tetrachloride; zinc In tetrahydrofuran at 20℃; for 0.0833333 h; Inert atmosphere General procedure: TiCl4 (0.7 mL, 6 mmol)was added to a stirred suspension of Zn powder (0.78 g, 12 mmol) in freshlydistilled anhydrous THF (15 mL) at room temperature (rt) under a dry N2atmosphere. After completion of the addition, the mixture was refluxed for 2 h.The suspension of the low-valent titanium reagent thus-formed was cooled tort. A solution of isatin or its derivatives 1 or 3 (2 mmol) in THF (10 mL) wasadded dropwise. The mixture was stirred at room temperature for about 5 minunder N2. After this period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture was quenchedwith 3percent HCl (15 mL) and extracted with CHCl3 (3 50 mL). The combinedextracts were washed with water (3 50 mL) and dried over anhydrousNa2SO4. After evaporation of the solvent under reduced pressure, the crudeproduct was purified by column chromatography (petroleum ether/ethylacetate = 5:1) to give the pure products 2 or 4.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 14, p. 2238 - 2242
[2] Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2033 - 2042
[3] Patent: US4658037, 1987, A,
[4] Patent: US4652658, 1987, A,
[5] Patent: US4730004, 1988, A,
[6] Patent: US4721712, 1988, A,
[7] Patent: US4725616, 1988, A,
[8] Patent: US4556672, 1985, A,
[9] Patent: US4569942, 1986, A,
[10] Patent: US4690943, 1987, A,
[11] Patent: EP208510, 1991, B1,
[12] Tetrahedron, 2011, vol. 67, # 5, p. 982 - 989
[13] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7349 - 7353
[14] Organic and Biomolecular Chemistry, 2015, vol. 13, # 22, p. 6371 - 6379
[15] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 1071 - 1082
  • 31
  • [ 6341-92-0 ]
  • [ 20776-61-8 ]
Reference: [1] Journal of Organic Chemistry, 1952, vol. 17, p. 149,153
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