CAS: 4005-49-6; N-(7H-Purin-6-yl)Benzamide

该化合物是一种合成的细胞素类比,广泛用于植物组织培养和农业研究,其主要优势在于能够促进细胞分裂和扩散,使其成为微质宣传和再生研究的宝贵工具.苯并聚物组比天然细胞素增强稳定性和生物活性,确保体外性能的一致性.该化合物在诱导芽和推迟植物组织中的耐性方面特别有效.其在有机溶剂中的溶解性以及与标准培养介质的兼容性进一步便利了实验应用.N6-Benzoyladeine是研究人员在受控植物生长系统中寻求可靠和高效细胞素活动的首选选择.

结构式图片

欧盟法规

ECHA物质C&L通报

上下游产品

CAS号98-88-4 苯甲酰氯 | CAS号66224-66-6 6H-Purin-6-imin... | CAS号188486-35-3 6-N-benzoyl-9-(... | CAS号188486-36-4 6-N-benzoyl-9-(... | CAS号188486-28-4 6-N-benzoyl-9-(... | CAS号4754-39-6 5'-脱氧腺苷 | CAS号4546-72-9 N-苯甲酰基-2'-脱氧腺苷 | CAS号18055-47-5 N-trimethylsily... | CAS号58-61-7 腺苷 | CAS号98983-40-5 9-(2-脱氧-2-氟-bet... | CAS号73-03-0 虫草素 | CAS号3228-71-5 2-(6-aminopurin... | CAS号14365-45-8 9-(2-脱氧-β-L-呋喃核... | CAS号17434-50-3 6-(6-aminopurin... | CAS号171406-46-5 ethyl 2-(6-benz...

合成工艺路线路线简述

  • 合成目标产物 N-Benzoylaminopurine 主要起始原料 Benzamide, N-[9-[3-C-Ethenyl-3,5-O-(1-Methylethylidene)-β-D-Xylofuranosyl]-9H-Purin-6-Yl]-
  • (文献来源)合成步骤主要原料 Benzamide, N-[9-[3-C-Ethenyl-3,5-O-(1-Methylethylidene)-β-D-Xylofuranosyl]-9H-Purin-6-Yl]-
6-N-Benzoyl-9-(3,5-O-Isopropylidene-3-C-Vinyl-β-D-Xylofuranosyl)Adenine置于吡啶,Potassium Permanganate,Phosphate Buffer,氘代甲醇,水,氘代三正丁基锡,臭氧,二氯磷酸苯酯,三乙胺,三氟乙酸体系中,用 四氢呋喃,二氯甲烷,水,叔丁醇 作为反应溶剂,化学反应 7.5H,反应生成 N6-苯甲酰基腺嘌呤
参考文献:Studies On The Mechanism Of Ribonucleotide Reductases
标题:Studies On The Mechanism Of Ribonucleotide Reductases
摘要:Ribonucleotide Reductases Are Enzymes That Catalyze The Conversion Of Ribonucleotides To 2'-Deoxyribonucleotides. This Important Reaction Is Initiated By The Generation Of A C-3' Nucleotide Radical And Subsequent Loss Of The 2'-Hydroxyl Group. In Order To Model Certain Steps In This Mechanism,Selenol Ester 23 Was Prepared And Photolyzed Providing The First Selective Chemical Access To The 3'-Adenosyl Radical. From Product Analysis It Could Be Shown That Elimination Of The 2'-Oh Function Readily Takes Place Under General Base Catalysis. The Rate Coefficient For This Reaction Was Determined By Competition Kinetics To Be 1.5 . 10(6) S(-1) In The Presence Of 1 M Triethylammonium Acetate Buffer At Ph 7. Without Catalyst The Elimination Rate Is About 10(3) Times Slower. It Can Be Concluded That A Similar Mechanism Is Also Feasible For The Key Steps Of The Enzyme Catalyzed Reaction.
DOI:10.1021/ja962974Q

海关参考信息

专利信息


专利号:US-8138330-B2
优先权日:2006-09-11
标 题 :Process for the synthesis of oligonucleotides
发明人:LEUCK MICHAEL; WOLTER ANDREAS; STUMPE ALFRED
权利人:LEUCK MICHAEL; WOLTER ANDREAS; STUMPE ALFRED; SIGMA ALDRICH CO LLC
摘要:The present invention discloses novel methods for the synthesis of oligonucleotides with nucleoside phosphoramidites on solid supports. The methods comprise the stepwise chain assembly of oligonucleotides on supports with 5′-acyl phosphoramidites. The synthesis cycles consist of a front end deprotection step which is conducted with a solution of a primary amine or a phenolate, a phosphoramidite coupling step with a 5′-acyl nucleoside phosphoramidite in the presence of an activator, a phosphite oxidation step and an optional capping step. The novel methods improve the quality of synthetic oligonucleotides due to the irreversibility of the front end deprotection step, which prevents the formation of deletion sequences, and due to the avoidance of acidic reagents in the synthesis cycles, which prevent the formation of depurination side products. The invention further discloses novel nucleoside phosphoramidite compositions wherein the phosphoramidites carry acyl front end protective groups which are cleavable with primary amines or phenolates. The invention is applicable to the synthesis of oligodeoxyribonucleotides, oligoribonucleotides and oligonucleotides with modifications in their sugar or phosphate groups.

专利号:US-2024287520-A1
优先权日:2021-06-30
标题:Method for synthesis of linkage modified oligomeric compounds
发明人:RODRIGUEZ ANDREW A
权利人:IONIS PHARMACEUTICALS INC
摘要:The present disclosure provides methods of synthesizing modified oligonucletodies and oligomeric compounds (including oligomeric compounds that are antisense agents or portions thereof) comprising a modified oligonucleotide having at least one modified internucleoside linking group. In certain embodiments, the present disclosure provides stabilized formulations of certain sulfonyl azides for use in the synthesis of olignonucleotides comprising one or more sulfonyl phosphoramidate linkages. Some embodiments provide stabilized compositions of high energy reagents that may be used in the synthesis of modified oligonucleotides, allowing for safe process scale preparation thereof.

专利号:US-10751419-B2
优先权日:2014-05-01
标题:Method for synthesis of reactive conjugate clusters
发明人:MIGAWA MICHAEL T; YU JINGHUA; WAN W BRAD; PATEL SAYTEN P; VASQUEZ GUILLERMO; KINBERGER GARTH A; PRAKASH THAZHA P; SETH PUNIT P; SWAYZE ERIC E
权利人:IONIS PHARMACEUTICALS INC
摘要:Provided herein are improved methods for the synthesis of reactive conjugate clusters and intermediates used in such methods. In particular, improvements are provided that enhance the synthesis of reactive conjugate clusters by reducing the number of synthetic steps required. The reactive conjugate clusters prepared using the improved methods don't include any transacylation impurities that are formed using existing methods. The improved methods also provide an increase in overall yield and a cost benefit over existing methods.

专利号:WO-9517903-A1
优先权日:1993-12-28
标 题:Modular design and synthesis of oxazolone-derived molecules
发明人:HOGAN JOSEPH C JR; CASEBIER DAVID; FURTH PAUL; TU CHENG
权利人:ARQULE PARTNERS L P; HOGAN JOSEPH C JR; CASEBIER DAVID; FURTH PAUL; TU CHENG
摘要:The design and synthesis of novel oxazolone-derived molecular modules and the use of the modules in the construction of new molecules and fabricated materials is disclosed. The new molecules and fabricated materials are molecular recognition agents useful in the design and synthesis of drugs, and have applications in separations and materials science.

专利号:EP-1108724-B1
优先权日:1996-01-16
标题 :Synthesis of methoxy nucleosides and enzymatic nucleic acid molecules
发明人:WINCOTT FRANCINE; BEIGELMANN LEONID; MATULIC-ADAMIC JASENKA; USMAN NASSIM; HAEBERLI PETER; KARPEISKY ALEXANDER; SWEEDLER DAVID; JARVIS THALE; DIRENZO ANTHONY
权利人:SIRNA THERAPEUTICS INC
摘要:This invention relates to chemical synthesis of 2'-O-methyl, 3'-O-methyl and 5'-O-methyl nucleosides, incorporation of novel chemical modifications in enzymatic nucleic acid molecules and improved methods for the synthesis of enzymatic nucleic acid molecules.

专利号:US-6639059-B1
优先权日:1999-03-24
标 题 :Synthesis of [2.2.1]bicyclo nucleosides
发明人:KOCHKINE ALEXEI; FENSHOLDT JEF; PFUNDHELLER HENRIK M
权利人:EXIQON AS
摘要:A synthesis of [2.2.1]bicyclo nucleosides which is shorter and provides higher overall yields proceeds via the key intermediate of the general formula III, wherein R4 and R5 are, for instance, sulfonates and R7 is, for instance, a halogen or an acetate. From compounds of the general formula II, such as 3-O-aryl-4-C-hydroxymethyl-1,2-O-isopropylidene-alpha-D-ribofuranose, intermediates of the general formula III are suitable for coupling with silylated nucleobases. Upon one-pot base-induced ring-closure and desulfonation of the formed [2.2.1]bicyclo nucleoside, a short route to each the LNA (Locked Nucleic Acid) derivatives of adenosine, cytosine, uridine, thymidine and guanidine is demonstrated. The use of the 5'-sulfonated ring-closed intermediate also allows for synthesis of 5'-amino- and thio-LNAs.
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主要参考文献

[参考文献]: M Kuwahara, Et Al. Synthesis Of Oxy-Peptide Nucleic Acids With Mixed Sequences. Nucleic Acids Symp Ser. 1999:(42):31-2.
[参考文献]: U Henriksen, Et Al. Facile Synthesis Of N-(1-Alkenyl) Derivatives Of 2,4-Pyrimidinediones. Nucleosides Nucleotides Nucleic Acids. 2000 Jul;19(7):1093-100.

合成参考文献


参考文献:10.1038/nchem.1506
摘要:Over B, Wetzel S, Grütter C, Nakai Y, Renner S, Rauh D, Waldmann H. Natural-product-derived fragments for fragment-based ligand discovery. Nat Chem. 2013 Jan;5(1):21–8. doi: 10.1038/nchem.1506.
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