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【结 构 式】 
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【分子编号】21843 【品名】tert-butyl [(tert-butoxycarbonyl)amino]carbothioylcarbamate 【CA登记号】145013-05-4 |
【 分 子 式 】C11H20N2O4S 【 分 子 量 】276.35688 【元素组成】C 47.81% H 7.29% N 10.14% O 23.16% S 11.6% |
合成路线1
该中间体在本合成路线中的序号：(XI)The hydroboration of allyl bromide (I) with diisopinocampheylborane gives the 3-bromopropylboronic ester (II), which by treatment with acetaldehyde and water yields the boronic acid (III). The reaction of (III) with NaN3 and ethanol affords 3-azidoboronic acid ethyl ester (IV), which is transesterified with optically active pipanediol (V) giving the cyclic ester (VI). The homologation of (VI) with LDA, ZnCl2 and dichloromethane in THF yields the alpha-chlorobutylboronic ester (VII), which is aminated with hexamethyldisylazane (HMDS) and BuLi to provide the silylated alpha-aminoboronic ester (VIII). The desilylation of (VIII) with methanol, and its protection with benzyl chloroformate gives the protected alpha-aminoboronic ester (IX). The hydrogenation of the azido group of (IX) with H2 over PtO2 affords the 4-aminobutylboronic ester (X), which is treated with N,N'-bis(tert-butoxycarbonyl)thiourea (XI), HgCl2 and TEA in DMF to give the guanidine derivative (XII). Finally, this compound is hydrolyzed and deprotected with refluxing 6N HCl.
| 【1】 Lebarbier, C.; Carreaux, F.; Carboni, B.; Boucher, J.L.; Synthesis of boronic acid analogs of L-arginine as alternate substrates or inhibitors of nitric oxide synthase. Bioorg Med Chem Lett 1998, 8, 18, 2573. |
| 【2】 Lebarbier, C.; et al.; Synthesis of a boronic acid analogue of L-ornithine. Synthesis 1996, 1371. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10101 | Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene | 501-53-1 | C8H7ClO2 | 详情 | 详情 | |
| (I) | 11463 | 3-Bromo-1-propene; 3-Bromopropene；allyl bromide | 106-95-6 | C3H5Br | 详情 | 详情 |
| (II) | 36654 | bis[[(1R,2S,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]methyl] 3-bromopropylboronate | C25H44BBrO2 | 详情 | 详情 | |
| (III) | 36655 | 3-bromopropylboronic acid | C3H8BBrO2 | 详情 | 详情 | |
| (IV) | 36656 | diethyl 3-azidopropylboronate | C7H16BN3O2 | 详情 | 详情 | |
| (V) | 32535 | (1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol | C10H18O2 | 详情 | 详情 | |
| (VI) | 36657 | 3-[(1S,2R,6S,8S)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]propyl azide; (1S,2R,6S,8S)-4-(3-azidopropyl)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]decane | C13H22BN3O2 | 详情 | 详情 | |
| (VII) | 36658 | (4S)-4-chloro-4-[(1S,2R,6S,8S)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butyl azide; (1S,2R,6S,8S)-4-[(1S)-4-azido-1-chlorobutyl]-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]decane | C14H23BClN3O2 | 详情 | 详情 | |
| (VIII) | 36659 | N-[(1R)-4-azido-1-[(1S,2R,6S,8S)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butyl](trimethyl)-N-(trimethylsilyl)silanamine; N-[(1R)-4-azido-1-[(1S,2R,6S,8S)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butyl]-N,N-bis(trimethylsilyl)amine | C20H41BN4O2Si2 | 详情 | 详情 | |
| (IX) | 36660 | benzyl (1R)-4-azido-1-[(1S,2R,6S,8S)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butylcarbamate | C22H31BN4O4 | 详情 | 详情 | |
| (X) | 36661 | benzyl (1R)-4-amino-1-[(1S,2R,6S,8S)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butylcarbamate | C22H33BN2O4 | 详情 | 详情 | |
| (XI) | 21843 | tert-butyl [(tert-butoxycarbonyl)amino]carbothioylcarbamate | 145013-05-4 | C11H20N2O4S | 详情 | 详情 |
| (XII) | 36662 | benzyl (1R)-4-([[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl]amino)-1-[(1S,2R,6S,8S)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butylcarbamate | C33H51BN4O8 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IX)N-Boc-Phenylalanine (I) was treated with isobutyl chloroformate and N-methylmorpholine, and the resulting mixed anhydride (II) was coupled to 2-aminobenzophenone (III) to yield the corresponding amide (IV). After Boc deprotection of (IV) with HCl in EtOAc, the intermediate aminoketone was cyclized with NaOH to the benzodiazepine (V). Alkylation of (V) with 3-nitrobenzyl bromide (VI) in the presence of t-BuOK in THF gave the (nitrobenzyl)benzodiazepine (VII). The nitro group of (VV) was subsequently reduced with SnCl2 in boiling EtOAc to affford (VIII). Then, the resulting amine (VIII) was treated with N,N'-di-Boc-thiourea (IX) in the presence of HgCl2 to provide the diprotected guanidine (X), which was finally deprotected with trifluoroacetic acid in CH2Cl2.
| 【1】 Dziadulewicz, E.K.; et al.; The design of non-peptide human bradykinin B2 receptor antagonists employing the benzodiazepine peptidomimetic scaffold. Bioorg Med Chem Lett 1999, 9, 3, 463. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 21835 | N-(tert-butoxycarbonyl)phenylalanine | 4530-18-1 | C14H19NO4 | 详情 | 详情 |
| (II) | 21836 | N-(Tert-butoxycarbonyl)-DL-phenylalanine isobutoxycarbonyl anhydride | C19H27NO6 | 详情 | 详情 | |
| (IV) | 21838 | tert-butyl 2-(2-benzoylanilino)-1-benzyl-2-oxoethylcarbamate | C27H28N2O4 | 详情 | 详情 | |
| (V) | 21839 | 3-benzyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one | C22H18N2O | 详情 | 详情 | |
| (VI) | 19636 | 1-(bromomethyl)-3-nitrobenzene | 3958-57-4 | C7H6BrNO2 | 详情 | 详情 |
| (VII) | 21841 | 3-benzyl-1-(3-nitrobenzyl)-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one | C29H23N3O3 | 详情 | 详情 | |
| (VIII) | 21842 | 1-(3-aminobenzyl)-3-benzyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one | C29H25N3O | 详情 | 详情 | |
| (IX) | 21843 | tert-butyl [(tert-butoxycarbonyl)amino]carbothioylcarbamate | 145013-05-4 | C11H20N2O4S | 详情 | 详情 |
| (X) | 21844 | tert-butyl (Z)-[3-[(3-benzyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-1-yl)methyl]anilino][(tert-butoxycarbonyl)amino]methylidenecarbamate | C40H43N5O5 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(VII)The reaction of imidazole (I) with tert-butoxycarbonyl anhydride in ethyl acetate, followed by acetylation with acetic anhydride gives the cis-ethylenediamine derivative (II), which is isomerized to its trans isomer (III) with I2 in THF. The cyclization of (III) with hydrazone (IV) by means of Na2CO3 in hot acetonitrile yields the tetrahydropyridazine (V), which s deprotected at the amino group with HCl in ethyl acetate affording the amine (VI). The condensation of (VI) with the protected thiourea (VII) by means of HgCl2 and Et3N in DMF gives the protected guanidine (VIII), which is hydrolyzed at the ester group with KOH in methanol/water providing the carboxylic acid (IX). Finally, this compound is deprotected with TFA in dichloromethane. The intermediate, the hydrazone derivative (IV) has been obtained by condensation of 2-ethylbutyryl hydrazide (X) with 3-bromo-2-oxobutyric acid ethyl ester in ethyl ether catalyzed by acetic acid.
| 【1】 Graves, B.J.; Zhang, L.; Escarpe, P.A.; Mendel, D.B.; Wang, K.-Y.; Chen, X.; Kim, C.U.; Williams, M.A.; Lawton, G.; Synthesis and evaluation of 1,4,5,6-tetrahydropyridazine derivatives as influenza neuraminidase inhibitors. Bioorg Med Chem Lett 1999, 9, 13, 1751. |
| 【2】 Zhang, L.; et al.; Synthesis and evaluation odf tetrahydropyridazine derivatives as influenza neuraminidase inhibitors. 217th ACS Natl Meet (March 21 1999, Anaheim) 1999, Abst MEDI 183. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 10255 | Imidazole; 1H-Imidazole | 288-32-4 | C3H4N2 | 详情 | 详情 |
| (II) | 31874 | tert-butyl (Z)-2-(acetamido)ethenylcarbamate | C9H16N2O3 | 详情 | 详情 | |
| (III) | 31881 | tert-butyl (E)-2-(acetamido)ethenylcarbamate | C9H16N2O3 | 详情 | 详情 | |
| (IV) | 31875 | ethyl 3-bromo-2-[(Z)-2-(2-ethylbutanoyl)hydrazono]propanoate | C11H19BrN2O3 | 详情 | 详情 | |
| (V) | 31877 | ethyl (5S,6S)-6-(acetamido)-5-[(tert-butoxycarbonyl)amino]-1-(2-ethylbutanoyl)-1,4,5,6-tetrahydro-3-pyridazinecarboxylate | C20H34N4O6 | 详情 | 详情 | |
| (VI) | 31878 | ethyl (5S,6S)-6-(acetamido)-5-amino-1-(2-ethylbutanoyl)-1,4,5,6-tetrahydro-3-pyridazinecarboxylate | C15H26N4O4 | 详情 | 详情 | |
| (VII) | 21843 | tert-butyl [(tert-butoxycarbonyl)amino]carbothioylcarbamate | 145013-05-4 | C11H20N2O4S | 详情 | 详情 |
| (VIII) | 31879 | ethyl (5S,6S)-6-(acetamido)-5-([[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl]amino)-1-(2-ethylbutanoyl)-1,4,5,6-tetrahydro-3-pyridazinecarboxylate | C26H44N6O8 | 详情 | 详情 | |
| (IX) | 31880 | (5S,6S)-6-(acetamido)-5-([[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl]amino)-1-(2-ethylbutanoyl)-1,4,5,6-tetrahydro-3-pyridazinecarboxylic acid | C24H40N6O8 | 详情 | 详情 | |
| (X) | 31876 | 2-ethylbutanohydrazide | C6H14N2O | 详情 | 详情 | |
| (XI) | 25183 | ethyl 3-bromo-2-oxopropanoate;ethyl 3-bromopyruvate;Bromopyruvic acid ethyl ester;ethyl 3-bromopyruvate;ethyl bromopyruvate | 70-23-5 | C5H7BrO3 | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(V)Fischer indole cyclization of naltrexone (I) with 4-nitrophenylhydrazine (II) provided 5'-nitronaltrindole (III). Subsequent reduction of the nitro group of (III) by means of hydrazine hydrate and Raney Nickel gave the 5'-amino derivative (IV). Mercury-assisted condensation of (IV) with di(tert-butoxy-carbonyl)thiourea (V) afforded the protected guanidine (VI). Finally, the Boc groups of (VI) were cleaved by treatment with trifluoroacetic acid to furnish the title compound.
| 【1】 Jones, R.M.; Hjorth, S.A.; Schwartz, T.W.; Portoghese, P.S.; Mutational evidence for a common kappa antagonist binding pocket in the wild-type kappa and mutant mu[K303E] opioid receptors. J Med Chem 1998, 41, 25, 4911. |
| 【2】 Sercel, A.D.; Stevens, W.C. Jr.; Ingals, S.; et al.; Naltrindole analogs as potent and selective kappa-opioid receptor antagonists. 218th ACS Natl Meet (Aug 22 1999, New Orleans) 1999, Abst MEDI 267. |
| 【3】 Stevens, W.C.; Jones, R.M.; Subramanian, G.; Metzger, T.G.; Ferguson, D.M.; Portoghese, P.S.; Potent and selective indolomorphinan antagonists of the kappa-opioid receptor. J Med Chem 2000, 43, 14, 2759. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 25079 | (1S,5R,13R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10-trien-14-one; Naltrexone | 16590-41-3 | C20H23NO4 | 详情 | 详情 |
| (II) | 34400 | 1-(4-nitrophenyl)hydrazine; 4-Nitrophenylhydrazine | 100-16-3 | C6H7N3O2 | 详情 | 详情 |
| (III) | 34703 | (1S,2S,13R,21R)-22-(cyclopropylmethyl)-7-nitro-14-oxa-11,22-diazaheptacyclo[13.9.1.0(1,13).0(2,21).0(4,12).0(5,10).0(19,25)]pentacosa-4(12),5,7,9,15(25),16,18-heptaene-2,16-diol | C26H25N3O5 | 详情 | 详情 | |
| (IV) | 34704 | (1S,2S,13R,21R)-7-amino-22-(cyclopropylmethyl)-14-oxa-11,22-diazaheptacyclo[13.9.1.0(1,13).0(2,21).0(4,12).0(5,10).0(19,25)]pentacosa-4(12),5,7,9,15(25),16,18-heptaene-2,16-diol | C26H27N3O3 | 详情 | 详情 | |
| (V) | 21843 | tert-butyl [(tert-butoxycarbonyl)amino]carbothioylcarbamate | 145013-05-4 | C11H20N2O4S | 详情 | 详情 |
| (VI) | 34705 | tert-butyl (Z)-[(tert-butoxycarbonyl)amino][[(1S,2S,13R,21R)-22-(cyclopropylmethyl)-2,16-dihydroxy-14-oxa-11,22-diazaheptacyclo[13.9.1.0(1,13).0(2,21).0(4,12).0(5,10).0(19,25)]pentacosa-4(12),5,7,9,15(25),16,18-heptaen-7-yl]amino]methylidenecarbamate | C37H45N5O7 | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(II)The known acridine-purine hybrid molecule (I) was converted into the Boc-protected bisguanidine derivative (III) by reaction with bis(tert-butoxycarbonyl)thiourea (II) in the presence of HgCl2 and Et3N. Subsequent acidic cleavage of the Boc groups gave the title compound.
| 【1】 Belmont, P.; et al.; Abasic site recognition in DNA as a new strategy to potentiate the action of anticancer alkylating drugs?. J Med Chem 1999, 42, 25, 5153. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 40720 | N(1)-[2-(6-amino-9H-purin-9-yl)ethyl]-N(3)-[3-[(6-chloro-2-methoxy-9-acridinyl)amino]propyl]-1,3-propanediamine; N-[2-(6-amino-9H-purin-9-yl)ethyl]-N-[3-([3-[(6-chloro-2-methoxy-9-acridinyl)amino]propyl]amino)propyl]amine | C27H32ClN9O | 详情 | 详情 | |
| (II) | 21843 | tert-butyl [(tert-butoxycarbonyl)amino]carbothioylcarbamate | 145013-05-4 | C11H20N2O4S | 详情 | 详情 |
| (III) | 40721 | tert-butyl (E,7E)-2-[2-(6-amino-9H-purin-9-yl)ethyl]-1,7-bis[(tert-butoxycarbonyl)amino]-6-[3-[(6-chloro-2-methoxy-9-acridinyl)amino]propyl]-11,11-dimethyl-9-oxo-10-oxa-2,6,8-triaza-7-dodecen-1-ylidenecarbamate | C49H68ClN13O9 | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(II)Condensation of amine (I) with N,N’-di-Boc-thiourea (II) using HgCl2 and Et3N in DMF (1) or with di-Boc-amidinopyrazole (III) in THF gives the protected guanidine derivative (IV), which by deacetylation with methanolic sodium methoxide followed by saponification of the deacylated methyl pyranosoate (V) leads to the carboxylic acid (VI). Alternatively, acid (VI) is prepared by direct hydrolysis of compound (IV) by means of aqueous NaOH or K2CO3 in H2O/MeOH. After conversion of acid (VI) to the corresponding benzhydryl ester (VII) by treatment with diphenyldiazomethane and BF3·Et2O, selective acylation of the primary hydroxyl group with octanoyl chloride (VIII) and Et3N in CH2Cl2 yields the 9-octanoate ester (IX) (1). Finally, compound (IX) is deprotected by removal of N-Boc and O-benzhydryl protecting groups by treatment with trifluoroacetic acid in CH2Cl2, followed by basification of the obtained TFA salt with NaHCO3 (2-8). Scheme 1.
Alternatively, reaction of the 4-amino-5,6-dihydropyran derivative (X) with di-Boc-amidinopyrazole (III) provides the corresponding 4-guanidinodihydropyran, which is hydrolyzed with K2CO3 in MeOH/H2O to give carboxylic acid (VI). In an alternative strategy, carboxylic acid (VI) is prepared by hydrolysis of the 4-amino-5,6-dihydropyrancarboxylate ester (X) with NaOH followed by reaction with the amidinopyrazole derivative (III). Deprotection of di-Boc intermediate (VI) by stirring at 80 °C in MeOH gives laninamivir (XI), which is finally selectively acylated with trimethyl orthooctanoate (XII) in the presence of methanolic HCl. Laninamivir (XI) can also be obtained by hydrolysis of intermediate (X) with NaOH followed by reaction of the resulting free amine (XIII) with pyrazole-1-carboxamidine HCl (XIV) or, alternatively, by treatment of 4-amino-5,6-dihydropyran (X) with pyrazole-1-carboxamidine HCl (XIV), and then hydrolysis of the methyl ester with K2CO3 in MeOH (3). Scheme 1.
| 【1】 Honda, T., Kobayashi, Y., Masuda, T., Yamashita, M., Arai, M. (Daiichi Sankyo Co., Ltd.). Neuraminic acid derivatives, their preparation and their medical use. EP 0823428, JP 1998330373, JP 1999279059, JP 199927968. |
| 【2】 Murakami, M., Yamaoka, M., Honda, T., Watanabe, M. (Daiichi Sankyo Co., Ltd.). Hydrates and crystals of a neuraminic acid compound. EP 1277759, US 2003105158, US 6844363, WO 200108131. |
| 【3】 Nakamura, Y., Murakami, M., Yamaoka, M., Wakayama, M., Umeo, K. (Daiichi Sankyo Co., Ltd.). Method for manufacturing neuraminic acid derivatives. EP 2132191, JP 2010523472, WO 2008126943. |
| 【4】 Honda, T., Kubo, S., Masuda, T., Arai, M., Kobayashi, Y., Yamashita, M. Synthesis and in vivo influenza-inhibitory effect of ester prodrug of 4-guanadino-7-O-methyl-Neu5Ac2en. Bioorg Med Chem Lett 2009, 19(11): 2938-40. |
| 【5】 Honda, T., Masuda, T. Synthesis of 4-guanidino-7-modified-neu5Ac2en derivatives and their biological activities as influenza sialidase inhibitors. J Synth Org Chem Jpn 2009, 67(11): 1105. |
| 【6】 Yamashita, M., Kawaoka, Y. (University of Tokyo; Daiichi Sankyo Co., Ltd.). Drug for treatment of influenza. EP 2123271, WO 2008108323. |
| 【7】 Honda, T., Arai, M., Yamashita, M., Masuda, T., Kobayashi, Y. (Daiichi Sankyo Co., Ltd.). Neuraminic acid derivatives, their preparation and their medical use. US 6340702. |
| 【8】 Kobayashi, Y., Honda, T., Yamashita, M. (Daiichi Sankyo Co., Ltd.). Neuraminic acid derivatives, their preparation and their medical use. US 2002137791, US 6451766. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 65992 | C17H26N2O9 | 详情 | 详情 | ||
| (II) | 21843 | tert-butyl [(tert-butoxycarbonyl)amino]carbothioylcarbamate | 145013-05-4 | C11H20N2O4S | 详情 | 详情 |
| (III) | 29482 | N,N-bis-Boc-1-guanylpyrazole; tert-butyl (E)-[(tert-butoxycarbonyl)amino](1H-pyrazol-1-yl)methylidenecarbamate | 152120-54-2 | C14H22N4O4 | 详情 | 详情 |
| (IV) | 65993 | C27H44N4O13 | 详情 | 详情 | ||
| (V) | 65994 | C23H40N4O11 | 详情 | 详情 | ||
| (VI) | 65995 | C22H38N4O11 | 详情 | 详情 | ||
| (VII) | 65996 | C35H48N4O11 | 详情 | 详情 | ||
| (VIII) | 11123 | Octanoyl chloride; n-Caprylyl chloride;Capryloyl chloride | 111-64-8 | C8H15ClO | 详情 | 详情 |
| (IX) | 65997 | C43H62N4O12 | 详情 | 详情 | ||
| (X) | 65998 | C14H20N2O8 | 详情 | 详情 | ||
| (XI) | 65999 | Laninamivir; (4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid | 203120-17-6 | C13H22N4O7 | 详情 | 详情 |
| (XII) | 66000 | trimethyl orthooctanoate; 1,1,1-Trimethoxyoctane | 161838-87-5 | C11H24O3 | 详情 | 详情 |
| (XIII) | 66001 | (4S,5R,6R)-5-acetylamino-4-amino-6-[(1R,2R)-2,3-dihydroxy-1-methoxy-propyl]-5,6-dihydro-4H-pyran-2-carboxylic acid | 475483-21-7 | C12H20N2O7 | 详情 | 详情 |
| (XIV) | 15983 | 1H-pyrazole-1-carboximidamide | 4023-00-1 | C4H6N4 | 详情 | 详情 |