JATRORRHIZINE HCL(RG)

Jatrorrhizine chloride is a potent and orally active uptake-2 transporter inhibitor, it can be isolated from various Chinese medicinal plants[1]. Jatrorrhizine chloride exhibits a critical neuroprotective role in H2O2-induced apoptosis via inhibition of MAPK pathway in HT22 hippocampal neurons[2].

General procedure: To a stirred solution of JTH (100 mg, 0.29 mmol) in anhydrous CH3CN or DMF, K2CO3 (122 mg, 0.88 mmol) was added and heated to 70 °C. Then R1Br or benzyl chloroformate (2'4 eq) was added andstirred for 5'6 h. The mixture was cooled to precipitate completely, filtrated and washed by CH2Cl2 toafford compounds 5a'g.General procedure: To a stirred solution of JTH (100 mg, 0.29 mmol) in anhydrous CH3CN or DMF, K2CO3 (122 mg, 0.88 mmol) was added and heated to 70 °C. Then R1Br or benzyl chloroformate (2'4 eq) was added andstirred for 5'6 h. The mixture was cooled to precipitate completely, filtrated and washed by CH2Cl2 toafford compounds 5a'g.General procedure: To a stirred solution of JTH (100 mg, 0.29 mmol) in anhydrous CH3CN or DMF, K2CO3 (122 mg, 0.88 mmol) was added and heated to 70 °C. Then R1Br or benzyl chloroformate (2'4 eq) was added andstirred for 5'6 h. The mixture was cooled to precipitate completely, filtrated and washed by CH2Cl2 toafford compounds 5a'g.General procedure: To a stirred solution of JTH (100 mg, 0.29 mmol) in anhydrous CH3CN or DMF, K2CO3 (122 mg, 0.88 mmol) was added and heated to 70 °C. Then R1Br or benzyl chloroformate (2'4 eq) was added andstirred for 5'6 h. The mixture was cooled to precipitate completely, filtrated and washed by CH2Cl2 toafford compounds 5a'g.General procedure: To a stirred solution of JTH (100 mg, 0.29 mmol) in anhydrous CH3CN or DMF, K2CO3 (122 mg, 0.88 mmol) was added and heated to 70 °C. Then R1Br or benzyl chloroformate (2'4 eq) was added andstirred for 5'6 h. The mixture was cooled to precipitate completely, filtrated and washed by CH2Cl2 toafford compounds 5a'g.General procedure: To a stirred solution of JTH (100 mg, 0.29 mmol) in anhydrous CH3CN or DMF, K2CO3 (122 mg, 0.88 mmol) was added and heated to 70 °C. Then R1Br or benzyl chloroformate (2'4 eq) was added andstirred for 5'6 h. The mixture was cooled to precipitate completely, filtrated and washed by CH2Cl2 toafford compounds 5a'g.General procedure: To a stirred solution of JTH (100 mg, 0.29 mmol) in anhydrous CH3CN or DMF, K2CO3 (122 mg, 0.88 mmol) was added and heated to 70 °C. Then R1Br or benzyl chloroformate (2'4 eq) was added andstirred for 5'6 h. The mixture was cooled to precipitate completely, filtrated and washed by CH2Cl2 toafford compounds 5a'g. 2, 9, 10-Trimethoxy-3-ethyloxyformylmethylenoxy protoberberine chloride (5a). JTH (373 mg, 1 mmol) wastreated with ethyl bromoacetate (668 mg, 4 mmol) according to the general procedure to give thedesired product 5a. Yield: 35percent; yellow solid; m.p. 234'236 °C; 1H-NMR (500 MHz) delta 9.91 (s, 1H), 9.07(s, 1H), 8.23 (d, J = 10.0 Hz, 1H), 8.06'8.04 (m, 1H), 7.76 (s, 1H), 7.04 (s, 1H), 4.94 (t, J = 5.0 Hz, 2H), 4.92(s, 2H), 4.20 (dd, J = 5.0 Hz, J = 15.0 Hz, 2H), 4.10 (s, 3H), 4.08 (s, 3H), 3.97 (s, 3H), 3.19 (t, J = 5.0 Hz, 2H), 1.24 (t, J = 5.0 Hz, 3H). 13C-NMR (126 MHz) delta 168.2, 150.2, 149.5, 148.6, 145.4, 143.5, 137.4, 132.9, 128.2, 126.6, 123.3, 121.3, 112.0, 119.7, 112.4, 109.1, 64.9, 61.8, 60.7, 56.9, 56.1, 55.2, 25.7, 14.0. HRMS:calcd. for C24H26ClNO6 [M]+: 424.1755, found: 424.1751.

Jaztorrhizine is an alkaloid extract from the Berberidaceae family of plants displaying antioxidant activity.

Molecular Weight:373.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:373.1080858
Monoisotopic Mass:373.1080858
Topological Polar Surface Area:51.8
Heavy Atom Count:26
Complexity:461
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes