Cryptotanshinone
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Cryptotanshinone
structure -
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CAS No:
35825-57-1
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Formula:
C19H20O3
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Chemical Name:
Cryptotanshinone
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Synonyms:
Phenanthro[1,2-b]furan-10,11-dione,1,2,6,7,8,9-hexahydro-1,6,6-trimethyl-,(1R)-;Phenanthro[1,2-b]furan-10,11-dione,1,2,6,7,8,9-hexahydro-1,6,6-trimethyl-,(R)-;(1R)-1,2,6,7,8,9-Hexahydro-1,6,6-trimethylphenanthro[1,2-b]furan-10,11-dione;Cryptotanshinone;Cryptotanshinon;Tanshinone c;Cryototanshinone;(15R)-Cryptotanshinone;(1R)-1,6,6-Trimethyl-2,7,8,9-tetrahydro-1H-naphtho[1,2-g][1]benzofuran-10,11-dione;4733-35-1
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CAS No:
Description
Cryptotanshinone is a natural compound extracted from the root of Salvia miltiorrhiza Bunge that shows antitumor activities. Cryptotanshinone inhibits STAT3 with an IC50 of 4.6 μM.
Cryptotanshinone is an abietane diterpenoid. It has a role as an anticoronaviral agent.
Characteristics
43.4
3.8
orange-brown
1.2±0.1 g/cm3
182 °C
459°C at 760 mmHg
203.4±28.8 °C
1.603
DMSO: ≥5mg/mL
Store at RT
168 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
Safety Information
Ⅲ
6.1
UN2811 - class 6.1 - PG 3 - EHS - Toxic solids, organic, n.o.s., HI: all
3
25-50/53
45-60-61
SF8282645
T,N
P273-P301 + P310-P501
H301-H410
|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P273, P301+P310, P321, P330, P391, P405, and P501|Aggregated GHS information provided by 196 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Cryptotanshinone Use and Manufacturing
General procedure: To a solution of tanshinones (0.1 mmol) in EtOH (0.1 M) was added diamine (0.15 mmol, 1.5 eq.) The solution was heated to reflux overnight. After TLC monitoring showed the completion of the reaction, the solvent was evaporated and the residue was subjected to PTLC isolation (Pet/CH2Cl2=5/1).General procedure: Solution of tanshinones (0.1 mmol), aryl aldehyde (0.2 mmol, 2 eq) and aminoacetate (0.4 mmol, 4 eq) in EtOH (0.1 M) was heated to reflux for 6 hours. After TLC monitoring showed the completion of the reaction, the solvent was evaporated and the residue was subjected to PTLC isolation (Pet/EtOAc=2/1).General procedure: Solution of tanshinones (0.1 mmol), aryl aldehyde (0.2 mmol, 2 eq) and aminoacetate (0.4 mmol, 4 eq) in EtOH (0.1 M) was heated to reflux for 6 hours. After TLC monitoring showed the completion of the reaction, the solvent was evaporated and the residue was subjected to PTLC isolation (Pet/EtOAc=2/1).General procedure: Solution of tanshinones (0.1 mmol), aryl aldehyde (0.2 mmol, 2 eq) and aminoacetate (0.4 mmol, 4 eq) in EtOH (0.1 M) was heated to reflux for 6 hours. After TLC monitoring showed the completion of the reaction, the solvent was evaporated and the residue was subjected to PTLC isolation (Pet/EtOAc=2/1).General procedure: To a solution of tanshinones (0.1 mmol) in EtOH (0.1 M) was added methylamine or ethylamine (0.2 mmol, 2 eq.) The solution was elevated to reflux overnight. After TLC monitoring showed the completion of the reaction, the solvent was evaporated and the residue was subjected to PTLC isolation (Pet/EtOAc=6/1). (2a) yellow amorphous, 76% yield.1H NMR (400 MHz, CDCl3) delta 7.85 (d, J = 8.8 Hz, 1H), 7.50 (d, J = 8.8 Hz, 1H), 4.91 (t, J = 9.0 Hz, 1H), 4.38 (q, J = 8.5 Hz, J = 6.3 Hz, 1H), 4.04 (m, 1H), 3.44 (t, J = 6.1 Hz, 2H), 2.73 (s, 3H), 1.98 (m, 2H), 1.77 (m, 2H), 1.52 (d, J = 6.8 Hz, 3H), 1.38 (s, 3H), 1.37 (s, 3H). EIMS m/z 321 [M]+. reaction flask was added (149mg, 0.5mmol), 2- fluorobenzaldehyde (65mg, 0.50mmol), 3ml of glacial acetic acid, ammonium acetate (0.77g, 10mmol), the reaction at 100-105C for 3-5 hours, after completion of the reaction, the mixture was cooled to room temperature, added 10ml of distilled water, concentrated aqueous ammonia adjust PH = about 7, filtered, washed with water, and dried to prepare a silica gel column chromatography to give a bright yellow powder, as the target product, yield 61.6% reaction flask was added (149mg, 0.5mmol), 3- fluorobenzaldehyde (130mg, 1.0mmol), 15ml glacial acetic acid, ammonium acetate (2.0g, 26mmol), the reaction at 100-105C for 3-5 hours, after completion of the reaction, the mixture was cooled to room temperature, added 30ml of distilled water, concentrated aqueous ammonia adjust PH = about 7, filtered, washed with water, and dried to prepare a silica gel column chromatography to give a bright yellow powder, as the target product, yield 55.8%,
inhibits angiogenesis
Computed Properties
Molecular Weight:296.4
XLogP3:3.8
Hydrogen Bond Acceptor Count:3
Exact Mass:296.14124450
Monoisotopic Mass:296.14124450
Topological Polar Surface Area:43.4
Heavy Atom Count:22
Complexity:571
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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