38691-95-1

Usage

Uses

Used in Pharmaceutical Industry:
Tetrahydricheilanthifolinium is used as a natural painkiller for its potential to alleviate pain without the need for synthetic opioids, offering a safer alternative for pain management.
Used in Neurological Applications:
In the field of neurology, Tetrahydricheilanthifolinium is used as a modulator of neurotransmitter levels, potentially aiding in the treatment of neurological disorders such as addiction, anxiety, and depression.
Used in Anti-inflammatory Applications:
Tetrahydricheilanthifolinium is utilized for its anti-inflammatory properties, which may help in reducing inflammation and associated symptoms in various conditions.
Used in Oncology:
In oncology, Tetrahydricheilanthifolinium is studied for its anti-cancer properties, with potential applications in the development of novel cancer therapies.
Used in Drug Development Research:
Tetrahydricheilanthifolinium is used as a subject of scientific research to explore its mechanisms of action and potential side effects, with the aim of developing it into a safe and effective therapeutic agent for various medical conditions.

InChI:InChI=1/C19H15NO4/c1-22-18-8-13-12(7-16(18)21)4-5-20-9-14-11(6-15(13)20)2-3-17-19(14)24-10-23-17/h2-3,6-9H,4-5,10H2,1H3/p+1

Synthetic route

C27H25NO6 → dehydrocheilanthifoline (38691-95-1)

Conditions	Yield
Stage #1: C27H25NO6 With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃; for 6h; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 2h;	82%

C9H6ClNO2 → dehydrocheilanthifoline (38691-95-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / dimethyl sulfoxide / 90 °C / Inert atmosphere 2.1: sodium carbonate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / toluene; ethanol / 12 h / 110 °C / Inert atmosphere 3.1: triethylamine; methanesulfonyl chloride / dichloromethane / 6 h / 20 °C 3.2: 2 h / 20 °C View Scheme

7-chloro-[1,3]dioxolo[4,5-h]isoquinoline → dehydrocheilanthifoline (38691-95-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium carbonate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / toluene; ethanol / 12 h / 110 °C / Inert atmosphere 2.1: triethylamine; methanesulfonyl chloride / dichloromethane / 6 h / 20 °C 2.2: 2 h / 20 °C View Scheme

C10H8ClNO2 → dehydrocheilanthifoline (38691-95-1)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: boron tribromide / dichloromethane / 2 h / -78 - -30 °C / Inert atmosphere 2.1: potassium carbonate / dimethyl sulfoxide / 90 °C / Inert atmosphere 3.1: sodium carbonate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / toluene; ethanol / 12 h / 110 °C / Inert atmosphere 4.1: triethylamine; methanesulfonyl chloride / dichloromethane / 6 h / 20 °C 4.2: 2 h / 20 °C View Scheme

UDP-glucose (133-89-1) + dehydrocheilanthifoline (38691-95-1) → C25H26NO9(1+)

Conditions	Yield
With Carthamus tinctorius UGT71AE1 In aq. buffer at 30℃; pH=7.4; Reagent/catalyst; Enzymatic reaction;

UDP-glucose (133-89-1) + dehydrocheilanthifoline (38691-95-1) → 7,8-dihydrogroenlandicine 3-O-β-D-glucopyranoside

Conditions	Yield
With Carthamus tinctorius UGT71AE1 In dimethyl sulfoxide at 30℃; pH=7.4; Enzymatic reaction;

Relevant academic research and scientific papers

Method for synthesizing benzophenanthridine and protoberberine alkaloids through modular diversity regulation and control

The invention discloses a method for synthesizing benzophenanthridine and protoberberine alkaloids through modular diversity regulation and control. The method comprises the following steps: improving a substituent group of a high-iodine salt leaving group, generating pyridine alkyne under the action of relatively mild potassium tert-butoxide, and carrying out [4 + 2] cycloaddition reaction on the pyridine alkyne and diene to obtain polysubstituted isoquinoline ring precursor compounds. Ring opening and aromatization of the isoquinoline ring precursor are realized by developing a novel iridium-catalyzed cross-coupling method, polysubstituted isoquinoline ring compounds with connecting capacity are efficiently synthesized, and then the polysubstituted isoquinoline ring compounds are coupled with a high-activity polysubstituted cyclic boric acid to obtain 3-aryl isoquinoline high-grade intermediates. Through application of two different chemical principles, regulation and control of the 3-aryl isoquinoline high-grade intermediates are realized, and benzophenanthridine and protoberberine alkaloids are modularly, diversely and efficiently synthesized.