1-iodo-2,4-dinitronaphthalene | 4112-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-iodo-2,4-dinitronaphthalene
• 英文别名: 1-iodo-2,4-dinitro-naphthalene；1-Jod-2,4-dinitro-naphthalin；1-Iod-2,4-dinitro-naphthalin (DNIN)；1-Iod-2,4-dinitro-naphthalin；1-Iod-2,4-dinitronaphthalin；1-Iod-2,4-dinitronaphtalin
• CAS: 4112-02-1
• 化学式: C₁₀H₅IN₂O₄
• 分子量: 344.065
• InChiKey: RTLODQZNHDPAGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-iodo-2,4-dinitronaphthalene 在 N-碘代丁二酰亚胺 、 sodium hydride 、 对甲苯磺酸 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 allyl-[3-(allyl-tert-butoxycarbonyl-amino)-4-iodo-naphthalen-1-yl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  3-取代的5-氨基-1-（氯甲基）-1，2-二氢-3H-苯并[e]吲哚（氨基-CBI）的新短合成。

  摘要：

  公开了一种来自Martius Yellow的3-取代的5-取代的5-氨基-1-（氯甲基）-1，2-二氢-3H-苯并[e]吲哚的新的短合成物。合成的关键步骤是三个有效的区域选择性反应（碘化，5-exo-trig芳基自由基-烯烃环化和羧化）。

  DOI：

  10.1021/jo0263115
• 作为产物：
  描述：

  氯硝萘 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-iodo-2,4-dinitronaphthalene
  参考文献：
  名称：

  403.在用溴或碘代替重氮基团时防止重氮氧化物的形成

  摘要：

  DOI：

  10.1039/jr9630002151

文献信息

• Reaction of Benzanthrone (7<i>H</i>-Benz[<i>d</i>,<i>e</i>]anthracen-7-one) with Nitrogen Dioxide Alone or in Admixture with Ozone. Implications for the Atmospheric Formation of Genotoxic 3-Nitrobenzanthrone
  作者：Takeji Enya、Hitomi Suzuki、Yoshiharu Hisamatsu

  DOI：10.1246/bcsj.71.2221

  日期：1998.9

  The reaction of benzanthrone (7H-benz[d,e]anthracen-7-one, 1) with nitrogen dioxide alone or in admixture with ozonized oxygen has been investigated in polar and nonpolar organic solvents at different temperatures. A remarkable change of product distribution was observed depending on the solvent employed; 3-nitrobenzanthrone (4) was the main product from the reaction in dichloromethane, while 2-nitrobenzanthrone

  苯并蒽酮 (7H-benz[d,e]anthracen-7-one, 1) 与二氧化氮单独或与臭氧化氧混合的反应已在极性和非极性有机溶剂中在不同温度下进行了研究。根据所使用的溶剂，观察到产物分布的显着变化；3-硝基苯蒽酮 (4) 是二氯甲烷中反应的主要产物，而 2-硝基苯蒽酮是四氯甲烷中的主要产物。发现加入质子酸或无机固体载体可促进反应，有利于前者硝基化合物的形成，而后者则以牺牲为代价。确定了所有主要产品。
• Observation by NMR of cationic Wheland-like intermediates in the deiodination of protected 1-iodonaphthalene-2,4-diamines in acidic media
  作者：Elvis A. Twum、Timothy J. Woodman、Wenyi Wang、Michael D. Threadgill

  DOI：10.1039/c3ob41386a

  日期：——

  1-Iodonaphthalene-2,4-diamines in trifluoroacetic acid/chloroform give stable Wheland-like tetrahedral cationic species observable by NMR, through an initial intramolecular protonation. Dynamic equilibria allow proton-deuterium exchange of aromatic protons and provide a mechanism for deiodination of 1-iodonaphthalene-2,4-diamines.

  在三氟乙酸/氯仿中，1-碘萘-2,4-二胺通过最初的分子内质子化作用，产生了可通过核磁共振观测到的稳定的惠兰四面体阳离子物种。动态平衡允许芳香质子进行质子-氘交换，为 1-碘萘-2,4-二胺的脱碘反应提供了一种机制。
• [EN] PROCESSES FOR PREPARING 3-SUBSTITUTED 1-(CHLOROMETHYL)-1,2-DIHYDRO-3H-[RING FUSED INDOL-5-YL(AMINE-DERIVED)] COMPOUNDS AND ANALOGUES THEREOF, AND TO PRODUCTS OBTAINED THEREFROM<br/>[FR] PROCEDE DE PREPARATION DE COMPOSES DE 3-SUBSTITUE 1-(CHLOROMETHYL)-1,2-DIHYDRO-3H [-5-YL A CYCLES FUSIONNES (DERIVES D'AMINE)] ET DE LEURS ANALOGUES, ET PRODUITS DERIVES
  申请人：AUCKLAND UNISERVICES LTD

  公开号：WO2003097635A1

  公开（公告）日：2003-11-27

  The invention provides processes of preparing 3-substituted 1-(chloromethyl)-1,2-dihydro-3H-[ring fused indol-5-yl(amine-derived)] compounds of formula (I) and its analogues, or a physiologically functional derivative thereof, (I), wherein A and B together may represent a fused optionally substituted benzene, naphthalene, pyridine, furan or a pyrrole ring, where the optional substituents are represented by Y; X is halogen or OSO2R , and W is selected from NO2, NHOH, N(R3)2NHR3, NHCO2R3, N(phthaloyl) or NH2, or W is further selected from the group (a) , wherein J is selected from OH or R, and P is a group which is a substrate suitable for a nitroreductase or carboxypeptidase enzyme. The invention is also directed to the use of compounds of formula (I) prepared by the processes of the invention as cytotoxins for cancer therapy and as prodrugs for gene-directed enzyme-prodrug therapy (GDEPT) and antibody-directed enzyme-prodrug therapy (ADEPT).

  该发明提供了制备公式（I）及其类似物的3-取代1-(氯甲基)-1,2-二氢-3H-[环融合吲哚-5-基（衍生自胺基）]化合物的过程，或其生理功能衍生物，其中A和B一起可以表示一个融合的可选取代苯、萘、吡啶、呋喃或吡咯环，其中可选取代基由Y表示；X为卤素或OSO2R，W从NO2、NHOH、N(R3)2NHR3、NHCO2R3、N(邻苯二甲酰基)或NH2中选择，或W进一步从群（a）中选择，其中J从OH或R中选择，P是适用于硝基还原酶或羧肽酶的底物基团。该发明还涉及通过该发明的过程制备的公式（I）化合物作为抗癌细胞毒素以及基因导向酶-前药疗法（GDEPT）和抗体导向酶-前药疗法（ADEPT）的前药的用途。
• Processes for preparing 3-substituted 1-(chloromethyl)-1,2-dihydro-3h-[ring fused indol-5-yl-(amine- derived)] compounds and analogues thereof, and to products obtained therefrom
  申请人：Denny Alexander William

  公开号：US20050148651A1

  公开（公告）日：2005-07-07

  The invention provides processes of preparing 3-substituted 1-(chloromethyl)-1,2-dihydro-3H-[ring fused indol-5-yl(amine-derived)] compounds of formula (I) and its analogues, or a physiologically functional derivative thereof, (I), wherein A and B together may represent a fused optionally substituted benezene, naphthalene, pyridine, furan or a pyrrole ring, where the optional substituents are represented by Y; X is halogen or OSO 2 R, and W is selected from NO 2 , NHOH, N(R 3 ) 2 NHR 3 , NHCO 2 R 3 , N(phthaloyl) or NH 2 , or W is further selected from the group (a), wherein J is selected from OH or R, and P is a group which is a substrate suitable for a nitroreductase or carboxypeptidase enzyme. The invention is also directed to the use of compounds of formula (I) prepared by the processes of the invention as cytotoxins for cancer therapy and as prodrugs for gene-directed enzyme-prodrug therapy (GDEPT) and antibody-directed enzyme-prodrug therapy (ADEPT).

  本发明提供了制备式(I)及其类似物或其生理功能衍生物的3-取代-1-(氯甲基)-1,2-二氢-3H-[环融合吲哚-5-基(氨基衍生)]化合物的过程，其中A和B在一起可以表示为融合的可选取代苯、萘、吡啶、呋喃或吡咯环，其中可选的取代基由Y表示；X是卤素或OSO2R，W从NO2、NHOH、N(R3)2NHR3、NHCO2R3、N(phthaloyl)或NH2中选择，或者W进一步从(a)组中选择，其中J从OH或R中选择，P是适用于硝基还原酶或羧肽酶酶的底物基团。本发明还涉及使用通过本发明的方法制备的式(I)化合物作为癌症治疗的细胞毒素以及基因导向酶前药治疗(GDEPT)和抗体导向酶前药治疗(ADEPT)的前药。
• Processes for preparing 3-substituted 1-(chloromethyl)-1,2-dihydro-3H-[ring fused indol-5-yl-(amine-derived)] compounds and analogues thereof, and to products obtained therefrom
  申请人：Auckland Uniservices Limited

  公开号：US07235578B2

  公开（公告）日：2007-06-26

  The invention provides processes of preparing 3-substituted 1-(chloromethyl)- 1,2-dihydro-3H-[ring fused indol-5-yl(amine-derived)] compounds of formula (I) and its analogues, or a physiologically functional derivative thereof, (I), wherein A and B together may represent a fused optionally substituted benezene, naphthalene, pyridine, furan or a pyrrole ring, where the optional substituents are represented by Y; X is halogen or OSO2R, and W is selected from NO2, NHOH, N(R3)2NHR3, NHCO2R3, N(phthaloyl) or NH2, or W is further selected from the group (a), wherein J is selected from OH or H, and P is a group which is a substrate suitable for a nitroreductase or carboxypeptidase enzyme. The invention is also directed to the use of compounds of formula (I) prepared by the processes of the invention as cytotoxins for cancer therapy and as prodrugs for gene-directed enzyme-prodrug therapy (GDEPT) and antibody-directed enzyme-prodrug theraphy (ADEPT).

  本发明提供了制备式(I)及其类似物或生理功能衍生物的3-取代-1-(氯甲基)-1,2-二氢-3H-[环融合吲哚-5-基(氨基衍生物)]化合物的过程，其中A和B可一起表示融合的可选取代苯、萘、吡啶、呋喃或吡咯环，其中可选的取代基由Y表示；X为卤素或OSO2R，且W从NO2、NHOH、N(R3)2NHR3、NHCO2R3、N(phthaloyl)或NH2中选择，或者W进一步从(a)组中选择，其中J从OH或H中选择，P是适用于硝基还原酶或羧肽酶酶的底物基团。本发明还涉及使用本发明的化合物(I)的制备过程作为癌症治疗的细胞毒素，以及作为基因定向酶前药治疗(GDEPT)和抗体定向酶前药治疗(ADEPT)的前药。