78155-76-7|5-Nitro-1H-indazole-3-carboxylic acid| Ambeed

Structure of 78155-76-7

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 78155-76-7 ] Purity: 95% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 78155-76-7 ]

CAS No. :	78155-76-7
Formula :	C₈H₅N₃O₄
M.W :	207.14
SMILES Code :	O=C(C1=NNC2=C1C=C([N+]([O-])=O)C=C2)O
MDL No. :	MFCD05663993
InChI Key :	MLTOGNYOQHDCAN-UHFFFAOYSA-N
Pubchem ID :	7144652

Safety of [ 78155-76-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 78155-76-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	5.0
Num. H-bond donors	2.0
Molar Refractivity	51.88
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	111.8 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.21
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.24
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.17
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.25
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.79
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.32

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.22
Solubility	1.26 mg/ml ; 0.00606 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.19
Solubility	0.135 mg/ml ; 0.000652 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.67
Solubility	4.41 mg/ml ; 0.0213 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.68 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	2.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.82

Application In Synthesis of [ 78155-76-7 ]

* 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.

Downstream synthetic route of [ 78155-76-7 ]

[ 78155-76-7 ] Synthesis Path-Downstream 1~35

1
[ 28284-09-5 ]
[ 78155-76-7 ]
[ 30962-81-3 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1990,vol. 26,p. 1146 - 1148.
Zhurnal Organicheskoi Khimii,1990,vol. 26,p. 1327 - 1330.

2
[ 78155-76-7 ]
[ 78155-77-8 ]

References: [1]Synthesis,2006,p. 1882 - 1894.
[2]Farmaco, Edizione Scientifica,1981,vol. 36,p. 315 - 333.

3
[ 4498-67-3 ]
[ 78155-76-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sulfuric acid; potassium nitrate; at 0 - 20℃; for 4h;	To a suspension of indazole-3-carboxylic acid 16AP (10.5g, 64.8mmol) in concentrated sulfuric acid (125ml) at OC was added KNO3 (64.8mmol, 6.55g). The reaction mixture was warmed up to r.t. After stirring for 4hr at r.t, it was poured into a 525ml of ice/water. Solid was collected by filtration and washed with water to give desired 5-nitro-1 H-indazole-3-carboxylic acid 17AP (10.74g, 80%).
63%	With sulfuric acid; nitric acid; at 10 - 20℃; for 1h;	At 10 C., indazole-3-carboxylic acid (0.3 g, 0.18) was dissolved in sulfuric acid (4 mL). Then a mixture of conc. sulfuric acid (2 mL) and 64% HNO3 (0.3 mL) was added and the mixture was allowed to warm to room temperature. After 1 h, the mixture was poured onto ice and water (30 mL). The resulting precipitate was filtered off and washed with cold H2O (2×20 mL). The crude product was recrystallized from AcOH to yield 0.17 g (63%). m.p. 189-194 C. 1H NMR (400 MHz, DMSO-d6) delta 14.3 (s, 1H), 9.37 (s, 1H), 8.38 (d, 1H), 7.69 (d, 1H), 6.9 (s, 1H).
	With sulfuric acid; potassium nitrate; at 0 - 20℃;Product distribution / selectivity;	To a suspension of indazoIe-3-carboxylic acid (compound 53, 3.0 g, 18 mmol) in 18 ml_ of concentrated sulfuric acid at 0 C was added potassium nitrate (2.0 g, 18 mmol). The reaction was stirred overnight at room temperature, poured into 150 mL of ice and extracted three times with ethyl acetate. The combined organic layer was washed with brine, dried and concentrated to give compound 54 (2.9 g) as the major isomer.; Step iTo a suspension of indazole-3-carboxylic acid (3.0 g, 18 rnmol) in 18 mL of concentrated sulfuric acid at 0 C was added potassium nitrate (2.0 g, 18 mmol). The reaction was stirred overnight at room temperature, poured into 150 mL of ice and extracted three times with ethyl acetate (90 mL total). The combined organic layer was washed with brine, dried and concentrated to give (54) (2.9 g) as the major product.; Step iTo a suspension of indazoIe-3-carboxylic acid (compound 53, 3.0 g, 18 mmol) in 18 mL of concentrated sulfuric acid at 0 C was added potassium nitrate (2.0 g, 18 mmol). The reaction was stirred overnight at room temperature, poured into 150 mL of ice and extracted three times with ethyl acetate. The combined organic layer was washed with brine, dried and concentrated to give compound 54 (2.9 g) as the major isomer.

References: [1]Patent: WO2008/153858,2008,A1 .Location in patent: Page/Page column 271.
[2]Patent: US2012/130078,2012,A1 .Location in patent: Page/Page column 7-8.
[3]Synthesis,2006,p. 1882 - 1894.
[4]Farmaco, Edizione Scientifica,1981,vol. 36,p. 315 - 333.
[5]Patent: WO2007/70398,2007,A1 .Location in patent: Page/Page column 217; 218; 220-221.

4
[ 78155-76-7 ]
[ 129295-49-4 ]
5-Nitro-1H-indazole-3-carboxylic acid (1-benzyl-4-methyl-[1,4]diazepan-6-yl)-amide [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1912 - 1930.

Yield	Reaction Conditions	Operation in experiment
	With water;Alkaline conditions;	Ethyl indazole-3-carboxylate (73.7 mmol) was dissolved in 20 mL concentrated sulfuric acid and the reaction mixture was cooled to 0 C. A mixture of concentrated sulfuric acid (12 mL) and 70% nitric acid (12 mL) was added dropwise over the course of 1 h. The mixture was stirred for an additional 1 h at 0 C and was poured onto of crushed ice (200 g). The solid was collected by vacuum filtration, washed with several portions of water and dried in vacuo. The dried solid was suspended in 250 mL acetonitrile and the mixture was heated at reflux for 2 h. The mixture was allowed to cool to room temperature and the solid was collected and dried in vacuo to provide ethyl 5- nitroindazole-3-carboxylate (53%) as a colorless solid. The acid, obtained by basic hydrolysis, was coupled with the bicyclobase according to procedure A.

6
[ 75-03-6 ]
[ 78155-76-7 ]
[ 1021389-35-4 ]

Yield	Reaction Conditions	Operation in experiment
35%	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 80℃; for 54h;	Example 26; 1-ethyl-5-(3-propyl-ureido)-1H-indazole-3-carboxylic acid (thiophen-2-ylmethyl)-amide; The title compound was prepared according to the procedure illustrated in schemes 3 and 6. Step 1. Iodoethane (11.6 mL, 145 mmol) was added to a suspension of <strong>[78155-76-7]5-nitro-1H-indazole-3-carboxylic acid</strong> (10.0 g, 48 mmol) and K2CO3 (20.3 g, 145 mmol) in dimethylformamide (100 mL). The reaction mixture was shaken at room temperature for 18 hours. Again, iodoethane (11.6 mL, 145 mmol) and K2CO3 (20.3 g, 145 mmol) were added to the reaction mixture and shaken for another 18 hours, then heated at 80 C. for a further 18 hours. The reaction mixture was saturated with water (300 mL) and extracted with dichloromethane (3×300 mL). The organic phases were combined and washed with brine (300 mL), dried over magnesium sulphate and concentrated in vacuo. The residue was purified by flash column chromatography (10% to 50% ethyl acetate/heptane) to afford 1-ethyl-<strong>[78155-76-7]5-nitro-1H-indazole-3-carboxylic acid</strong> ethyl ester, 4.45 g (35%). LC(at)215 nm; Rt 1.41: 94%, m/z (ES+): 264.2 (M+H).

References: [1]Patent: US2008/103182,2008,A1 .Location in patent: Page/Page column 16.

7
[ 78155-76-7 ]
5-nitro-1H-indazole-3-carboxylic acid chloride [ No CAS ]