38314-91-9

Usage

Chemical Class

Nitro compounds

Derivative

Nitro derivative of 9H-pyrido[3,4-b]indole

Substitution

Methyl group attached at the 1-position of the pyridine ring

Potential Activities

Anticancer agent, inhibition of cancer cell growth

Value in Synthesis

Valuable building block for the synthesis of other complex chemical compounds

Safety Precautions

Handle and store with care due to potential explosive properties

InChI:InChI=1/C12H9N3O2/c1-7-12-9(4-5-13-7)10-6-8(15(16)17)2-3-11(10)14-12/h2-6,14H,1H3

Upstream product

• 486-84-0 harmane 
• 2506-10-7 eleagnine 
• 61-54-1 tryptamine 
• 487-89-8 Indole-3-carboxaldehyde 
• 120-72-9 indole 
• 3156-51-2 3-[(E)-2-nitroeth-1-enyl]-1H-indole 
• 73-22-3 L-Tryptophan 

Downstream Products

• 102206-91-7 1-methyl-9H-β-carbolin-6-ylamine 
• 18813-71-3 6-bromo-1-methyl-9H-pyrido[3,4-b]indole 

Relevant academic research and scientific papers

Preparation method and application of 6-substituted-beta-carboline alkali compound and derivative

The invention relates to a preparation method and application of a 6-substituted-beta-carboline alkali compound and a derivative. The invention discloses a novel compound, namely the 6-substituted-beta-carboline alkali compound, and an application of the 6-substituted-beta-carboline alkali compound in a farm chemical bactericide. The invention also discloses the preparation method of the 6-substituted-beta-carboline alkali compound. The 6-substituted-beta-carboline alkali compound disclosed by the invention is a novel compound, has relatively good antibacterial activity and can be applied to farm chemical bactericides.

?-CARBOLINE, DIHYDRO-?-CARBOLINE AND TETRAHYDRO-?-CARBOLINE ALKALOID DERIVATIVES AND PREPARATION METHODS SAME AND USE IN ASPECTS OF PREVENTING AND TREATING PLANT VIRUSES, FUNGICIDES AND INSECTICIDES

The present invention relates to β-carboline, dihydro-β-carboline and tetrahydro-β-carboline alkaloid derivatives (I) and a method for preparing same and the use in the aspects of preventing and treating plant viruses, fungicides and insecticides. For the meaning of each group in formula (I) see the description. The β-carboline, dihydro-β-carboline and tetrahydro-β-carboline alkaloid derivatives of the present invention show a particularly ourstanding anti-plant virus activity, and also have fungicidal and insecticidal activities.

Synthesis and antiviral and fungicidal activity evaluation of β-carboline, dihydro-β-carboline, tetrahydro-β-carboline alkaloids, and their derivatives

Six known β-carboline, dihydro-β-carboline, and tetrahydro-β-carboline alkaloids and a series of their derivatives were designed, synthesized, and evaluated for their anti-tobacco mosaic virus (TMV) and fungicidal activities for the first time. All of the alkaloids and some of their derivatives (compounds 3, 4, 14, and 19) exhibited higher anti-TMV activity than the commercial antiviral agent Ribavirin both in vitro and in vivo. Especially, the inactivation, curative, and protection activities of alkaloids Harmalan (62.3, 55.1, and 60.3% at 500 μg/mL) and tetrahydroharmane (64.2, 57.2, and 59.5% at 500 μg/mL) in vivo were much higher than those of Ribavirin (37.4, 36.2, and 38.5% at 500 μg/mL). A new derivative, 14, with optimized physicochemical properties, obviously exhibited higher activities in vivo (50.4, 43.9, and 47.9% at 500 μg/mL) than Ribavirin and other derivatives; therefore, 14 can be used as a new lead structure for the development of anti-TMV drugs. Moreover, most of these compounds exhibited good fungicidal activity against 14 kinds of fungi, especially compounds 4, 7, and 11.

Synthesis and antiviral and fungicidal activity evaluation of β-carboline, dihydro-β-carboline, tetrahydro-β-carboline alkaloids, and their derivatives

Six known β-carboline, dihydro-β-carboline, and tetrahydro-β-carboline alkaloids and a series of their derivatives were designed, synthesized, and evaluated for their anti-tobacco mosaic virus (TMV) and fungicidal activities for the first time. All of the alkaloids and some of their derivatives (compounds 3, 4, 14, and 19) exhibited higher anti-TMV activity than the commercial antiviral agent Ribavirin both in vitro and in vivo. Especially, the inactivation, curative, and protection activities of alkaloids Harmalan (62.3, 55.1, and 60.3% at 500 μg/mL) and tetrahydroharmane (64.2, 57.2, and 59.5% at 500 μg/mL) in vivo were much higher than those of Ribavirin (37.4, 36.2, and 38.5% at 500 μg/mL). A new derivative, 14, with optimized physicochemical properties, obviously exhibited higher activities in vivo (50.4, 43.9, and 47.9% at 500 μg/mL) than Ribavirin and other derivatives; therefore, 14 can be used as a new lead structure for the development of anti-TMV drugs. Moreover, most of these compounds exhibited good fungicidal activity against 14 kinds of fungi, especially compounds 4, 7, and 11.

Reductive N -alkylation of nitroarenes: A green approach for the N-alkylation of natural products

A simple, mild, cost-effective, and green approach for the reductive mono-N-alkylation of nitroarenes has been developed. HOAc/Zn are utilized as the reducing system together with a carbonyl compound as an alkyl source in methanol. Excellent yields were obtained with stoichiometric control of mono- over dialkylated products. Application to five complex natural products demonstrated the practical utility of the method.

Reductive amidation of nitroarenes: a practical approach for the amidation of natural products

A simple and practical approach for the one-pot conversion of nitroarenes into amide derivatives has been developed. Zinc and acetic acid are utilized as a reducing agent, and acyl chloride and triethylamine are used as the acylating agent in DMF with good yield (～60%) of the amide. This method was applicable to manzamine A (1), where the yield of 6-cyclohexamidemanzamine A (7) was significantly improved (56%) by this approach relative to (17%) by beginning with the amine.

Synthesis and cytotoxic activity of pyridazino[1′,6′:1,2]pyrido[3,4-b]indol-5-inium derivatives as anti-cancer agents

Several new pyridazino[1′,6′:1,2]pyrido[3,4-b]indol-5-inium derivatives were synthesised from β-carboline derivatives and their cytotoxic activity and effect on the cell cycle were evaluated against L1210 cancer cells.

Synthesis and isolation of nitro-β-carbolines obtained by nitration of commercial β-carboline alkaloids

Nitration of commercial full aromatic β-carboline alkaloids nor-harmane (1), harmane (2), harmine (3), harmol (4), and the 7-acetylated derivative of harmol (5) is described. Advantages and disadvantages of different nitration reagents which involve acidic conditions (HNO3/H+) and neutral conditions (Cu(NO3)2; ceric ammonium nitrate) are discussed. A complete 1H and 13C-nmr characterization including ms and also uv absorption spectra in neutral and acid media is presented. A detailed ei-ms and ld-tof-ms study is enclosed because the nitro-β-carbolines constitute a new family of β-carboline-like chromophores with potential use as matrix in uv-maldi-tof-ms.