187865-22-1

Basic information

• Product Name: derquantel
• Synonyms: derquantel;2-Deoxoparaherquamide;Unii-0L0ugk6oox;2-DeoxoparaherquaMide, 2-DeoxoparaherquaMide A, 2-DesoxoparaherquaMide A, PF 00520904, PNU 141962
• CAS NO: 187865-22-1
• Molecular Formula: C₂₈H₃₇N₃O₄
• Molecular Weight: 479.617
• Mol File: 187865-22-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 641.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.34
• PKA: 15.18±0.60(Predicted)
• CAS DataBase Reference: derquantel(CAS DataBase Reference)
• NIST Chemistry Reference: derquantel(187865-22-1)
• EPA Substance Registry System: derquantel(187865-22-1)

Safety Data

• Hazardous Substances Data: 187865-22-1(Hazardous Substances Data)

Usage

Description

Derquantel is an anthelmintic spiroindole that acts as a nicotinic acetylcholine receptor antagonist, causing flaccid paralysis and expulsion of nematodes. It is a semi-synthetic paraherquamide analogue prepared by removal of the 2-oxo group in a four-step sequence of N-protection, reduction, N-deprotection, and a final reduction. Derquantel was the first paraherquamide to be successfully commercialized in combination with avermectin.

Uses

Used in Veterinary Medicine:
Derquantel is used as a potent nematocide for the treatment of gastrointestinal nematode parasites in sheep. It is particularly effective when combined with the macrocyclic lactone, abamectin, which results in synergistic anthelmintic effects against these parasites.
Used in Parasite Control:
Derquantel is used as an anthelmintic agent for controlling and eliminating nematode parasites in livestock, specifically in the agricultural industry. Its ability to induce flaccid paralysis in nematodes through the inhibition of nicotinic acetylcholine receptors makes it a valuable tool in maintaining the health of livestock and reducing the impact of parasitic infections on the farming sector.

Synthetic route

C28H35N3O4 (187865-16-3) → Derquantel (187865-22-1)

Conditions	Yield
With sodium tetrahydroborate In methanol at 0℃;	80%

Paraherquamide (77392-58-6) → Derquantel (187865-22-1)

Conditions	Yield
With lithium borohydride

C43H47N3O7 (187865-97-0) → Derquantel (187865-22-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: piperidine / tetrahydrofuran 2: 80 percent / NaBH4 / methanol / 0 °C View Scheme

Derquantel (187865-22-1) → 14,17-anhydro-2-desoxoparaherquamide A (512848-25-8)

Conditions	Yield
With dmap; diethylamino-sulfur trifluoride In dichloromethane at 20℃; for 1h;	50%

Derquantel (187865-22-1) → 14-oxo-2-desoxo-1,2-anhydro-17-norparaherquamide A (512848-29-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 50 percent / DMAP; (diethylamino)sulfurtrifluoride / CH2Cl2 / 1 h / 20 °C 2: 12 percent / osmium tetroxide; 4-methylmorpholine N-oxide / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 18 h / 5 °C 3: 41 percent / sodium periodate / tetrahydrofuran; H2O / 16 h / 5 °C View Scheme

Derquantel (187865-22-1) → 14-oxo-2-desoxo-17-norparaherquamide A (512848-28-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 50 percent / DMAP; (diethylamino)sulfurtrifluoride / CH2Cl2 / 1 h / 20 °C 2: 12 percent / osmium tetroxide; 4-methylmorpholine N-oxide / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 18 h / 5 °C 3: 41 percent / sodium periodate / tetrahydrofuran; H2O / 16 h / 5 °C 4: 50 percent / NaBH3CN / methanol / 0.5 h / 0 °C View Scheme
Multi-step reaction with 3 steps 1: 50 percent / DMAP; (diethylamino)sulfurtrifluoride / CH2Cl2 / 1 h / 20 °C 2: 25 percent / osmium tetroxide; 4-methylmorpholine N-oxide / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 18 h / 5 °C 3: 58 percent / sodium periodate / tetrahydrofuran; H2O / 16 h / 5 °C View Scheme

Derquantel (187865-22-1) → 17-hydroxy-2-desoxo-1,2-anhydroparaherquamide A (512848-27-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 50 percent / DMAP; (diethylamino)sulfurtrifluoride / CH2Cl2 / 1 h / 20 °C 2: 12 percent / osmium tetroxide; 4-methylmorpholine N-oxide / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 18 h / 5 °C View Scheme

Derquantel (187865-22-1) → 17-hydroxy-2-desoxoparaherquamide A (512848-26-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 50 percent / DMAP; (diethylamino)sulfurtrifluoride / CH2Cl2 / 1 h / 20 °C 2: 25 percent / osmium tetroxide; 4-methylmorpholine N-oxide / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 18 h / 5 °C View Scheme

Derquantel (187865-22-1) → [17-D3]-2-desoxoparaherquamide A

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 50 percent / DMAP; (diethylamino)sulfurtrifluoride / CH2Cl2 / 1 h / 20 °C 2.1: 12 percent / osmium tetroxide; 4-methylmorpholine N-oxide / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 18 h / 5 °C 3.1: 41 percent / sodium periodate / tetrahydrofuran; H2O / 16 h / 5 °C 4.1: tetrahydrofuran / 1 h / -78 - 0 °C 4.2: 50 percent / NaBH3CN / methanol / 0.5 h / 0 °C View Scheme
Multi-step reaction with 5 steps 1.1: 50 percent / DMAP; (diethylamino)sulfurtrifluoride / CH2Cl2 / 1 h / 20 °C 2.1: 12 percent / osmium tetroxide; 4-methylmorpholine N-oxide / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 18 h / 5 °C 3.1: 41 percent / sodium periodate / tetrahydrofuran; H2O / 16 h / 5 °C 4.1: 50 percent / NaBH3CN / methanol / 0.5 h / 0 °C 5.1: tetrahydrofuran / 1 h / -78 - 0 °C 5.2: 20 percent / NaBH3CN / methanol / 0.5 h / 0 °C View Scheme
Multi-step reaction with 4 steps 1.1: 50 percent / DMAP; (diethylamino)sulfurtrifluoride / CH2Cl2 / 1 h / 20 °C 2.1: 25 percent / osmium tetroxide; 4-methylmorpholine N-oxide / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 18 h / 5 °C 3.1: 58 percent / sodium periodate / tetrahydrofuran; H2O / 16 h / 5 °C 4.1: tetrahydrofuran / 1 h / -78 - 0 °C 4.2: 20 percent / NaBH3CN / methanol / 0.5 h / 0 °C View Scheme

Upstream product

• 187865-97-0 C₄₃H₄₇N₃O₇ 
• 187865-16-3 C₂₈H₃₅N₃O₄ 
• 77392-58-6 Paraherquamide 

Relevant articles and documents

Semi-synthesis of 2-deoxo- and 3-epi-paraherquamide A

2-Deoxo- and 3-epi-paraherquamide A were synthesized from paraherquamide A. 2-Deoxoparaherquamide A has good activity against HC and TC in our jird model comparable to the parent compound, while 3-epi-paraherquamide A showed no activity.