There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.
Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 51298-62-5 | MDL No. : | MFCD00039052 |
Formula : | C7H16ClN5O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QBNXAGZYLSRPJK-JEDNCBNOSA-N |
M.W : | 269.69 | Pubchem ID : | 135193 |
Synonyms : |
NG-Nitroarginine methyl ester hydrochloride;L-NAME (hydrochloride);H-Arg(NO2)-OMe.HCl;51298-62-5;N(G)-Nitro-L-arginine methyl ester;L-NG-Nitroarginine methyl ester;N-Nitro-L-arginine methylester;NG-Nitroarginine methyl ester;L-NAME HCl
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.71 |
Num. rotatable bonds : | 9 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 4.0 |
Molar Refractivity : | 64.02 |
TPSA : | 146.05 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.84 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 0.15 |
Log Po/w (WLOGP) : | -0.63 |
Log Po/w (MLOGP) : | -0.67 |
Log Po/w (SILICOS-IT) : | -3.04 |
Consensus Log Po/w : | -0.84 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.01 |
Solubility : | 26.2 mg/ml ; 0.0972 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.77 |
Solubility : | 0.454 mg/ml ; 0.00168 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -0.45 |
Solubility : | 96.6 mg/ml ; 0.358 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 5.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.01 |
Signal Word: | Danger | Class: | 4.1 |
Precautionary Statements: | P501-P261-P270-P240-P210-P241-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312 | UN#: | 1325 |
Hazard Statements: | H302+H312+H332-H315-H319-H228 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) Et3N, THF, DMF, CH2Cl2, (ii) /BRN= 1188572/, DCC; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dicyclohexyl-carbodiimide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With N-Ethylmaleimide; benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 25℃; for 18h; pH 7.0-7.5; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 22.5h; | |
90% | With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 22.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 24.5h; | |
64 mg | With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 22.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) triethylamine / dioxane / 1.) RT, 1 h, 2.) RT, 12 h 2: hydrogen, HCl / PdCl2 / methanol / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With sodium triacetoxyborohydride; acetic acid In N,N-dimethyl-formamide; toluene at 90℃; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Stage #1: 4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-3-methoxybenzoic acid; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; | Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Stage #1: C12H14O3; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; | Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: p-[(3,7-dimethyl-2,6-octadienyl)oxy]benzoic acid; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; | Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | Stage #1: p-isopentenoxybenzenepropanoic acid; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; | Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | Stage #1: 3-(4-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}phenyl)propanoic acid; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; | Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | Stage #1: 4'-Geranyloxyferulic acid; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; | Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Stage #1: C14H16O3; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; | Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | Stage #1: Geranyloxy-p-coumaric acid; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; | Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Stage #1: C13H16O4; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; | Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: C15H18O4; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; | Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: (E)-3-(3,5-dibromo-4-methoxyphenyl)acrylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.5h; Stage #2: nitro-L-arginine methyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 36h; | General procedure D for the synthesis of compound 9a. General procedure: To a stirred solution of the acid derivative 4b(100 mg, 0.241 mmol, 1.0 equiv) in anhydrous CH2Cl2 (4 mL) was added HOBT (72 mg, 0.530 mmol, 2.2equiv), EDC·HCl (103 mg, 0.530 mmol, 2.2 equiv). The solution was then stirred for 30 min at sametemperature. The resultant solution was then transferred to 0 °C and DIPEA (116 mg, 0.892 mmol, 3.0 equiv) was added dropwise to the solution followed by compound 8a (51 mg, 0.327 mmol, 1.1 equiv) andallowed to stirred for 36 h from 0 oC to rt. After completion of starting material, the reaction mixture wasquenched by adding 5 mL saturated aqueous NaHCO3 solution and the aqueous layer was extracted withCH2Cl2 (3 ×10 mL). The solution was then washed with brine, dried over Na2SO4 and concentrated underreduced pressure to afford the crude ester derivative of acid-amine coupling product. The crude amideproduct was directly subjected to ester hydrolysis using LiOH.H2O (2.0 equiv) in THF and H2O (0.5 mL)at room temperature for 4 h (TLC monitored). Then the volatile was evaporated under reduced pressure andH2O (2 mL) was added to the reaction mixture followed by 10% aqueous HCl was added with a maintainedPH = 2. Further, it was extracted with CH2Cl2 (2 ×10 mL). The solution was then washed with brine, driedover Na2SO4 and concentrated under reduced pressure to afford the crude acid derivative which was directlysubjected to column chromatography using 2-3% MeOH in DCM afforded the pure compound 9a in 84%yield as a white solid over two-steps. |