N,N-bis(2-hydroxyethyl)-2-nitroaniline | 7334-82-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-bis(2-hydroxyethyl)-2-nitroaniline
• 英文别名: N-(2-nitrophenyl)diethanolamine；2-nitro-[bis(2'-hydroxyethyl)]-aniline；N,N-Bis-(2-hydroxyethyl)-2-nitro-anilin, N-(2-Nitro-phenyl)-diethanolamin；2-[N-(2-hydroxyethyl)-2-nitroanilino]ethanol
• CAS: 7334-82-9
• 化学式: C₁₀H₁₄N₂O₄
• 分子量: 226.232
• InChiKey: RYTPTVAFWZRLJU-UHFFFAOYSA-N

物化性质

• 沸点：
  425.7±40.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  89.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-bis(2-hydroxyethyl)-2-nitroaniline 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 dibutyl laurate 、 triethylamine trihydrofluoride 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 di-tert-butyl 4-{[2'-(N,N-bis(2''-mesyloxyethyl)amino)phenyl]carbamoyloxymethyl}phenyloxycarbonyl-L-glutamate
  参考文献：
  名称：

  Self-Immolative Nitrogen Mustards Prodrugs Cleavable by Carboxypeptidase G2 (CPG2) Showing Large Cytotoxicity Differentials in GDEPT

  摘要：

  Nineteen novel potential self-immolative prodrugs and their corresponding drugs have been synthesized for gene-directed enzyme prodrug therapy (GDEPT) with carboxypeptidase G2 (CPG2) as the activating enzyme. The compounds are derived from o- and p-amino and p-methylamino aniline nitrogen mustards. Their aqueous stability, kinetics of drug release by CPG2, and cytotoxicity in the colon carcinoma cell line WiDr, expressing either surface-tethered CPG2 (stCPG2(Q)3) or control beta-galactosidase, are assessed. The effect of various structural features on stability, kinetics of activation, and biological activity is discussed. The p-methylamino prodrugs are the most stable compounds from this series, with the largest cytotoxicity differentials between CPG2-expressing and nonexpressing cells. The most potent compounds in all series are prodrugs of bis-iodo nitrogen mustards. 4-{N-[4'-Bis(2"-iodoethyl)aminophenyll-N'-methylcarbamoyloxymethyl}phenylcarbamoyl-L-glutamic acid, compound 39b, is 124-fold more cytotoxic to WiDr cells expressing CPG2 than to cells expressing beta-galactosidase. An additional six compounds show better cytotoxicity differential than the published N-{4-[(2-chloroethyl)(2-mesyloxyethyl)amino]benzoyl}-L-glutamic acid (CMDA) prodrug.

  DOI：

  10.1021/jm020462i
• 作为产物：
  描述：

  1-(2-Nitrophenyl)-2,5-dihydropyrrole 在 sodium periodate 、 四氧化锇 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 14.17h， 生成 N,N-bis(2-hydroxyethyl)-2-nitroaniline
  参考文献：
  名称：

  Palmer, Brian D; Denny, William A, Synthetic Communications, 1987, vol. 17, # 5, p. 601 - 610

  摘要：

  DOI：

文献信息

• Cationic diazo compounds, compositions comprising them as direct dye, process for dyeing keratin fibers and device therefor
  申请人：Greaves Andrew

  公开号：US20060005327A1

  公开（公告）日：2006-01-12

  The present disclosure relates to cationic diazo compounds chosen from those of formula (I) and the acid addition salts thereof: Dye1-LK-Dye2 (I); and to dye compositions comprising the the compounds as direct dye, and also to a process for dyeing keratin fibers using this composition and a multi-compartment device.

  本公开涉及选择自式(I)的阳离子重氮化合物及其酸盐：Dye1-LK-Dye2（I）；以及包含这些化合物作为直接染料的染料组合物，还涉及使用该组合物和多室装置染色角蛋白纤维的方法。
• [EN] ENZYME ACTIVATED SELF-IMMOLATIVE N-SUBSTITUTED NITROGEN MUSTARD PRODRUGS<br/>[FR] PROMEDICAMENTS ACTIVES PAR UNE ENZYME ET AUTO-IMMOLATEURS A BASE DE MOUTARDE D'AZOTE N-SUBSTITUTE
  申请人：CANCER REC TECH LTD

  公开号：WO2004020400A1

  公开（公告）日：2004-03-11

  This invention pertains to certain enzyme (CPG2) activated self-immolative nitrogen mustard prodrugs, which are useful in enzyme prodrug therapy (EPT), such as ADEPT and GDEPT, for the treatment of proliferative conditions, such as cancer, and which have the following formula: wherein RN is independently C1-7alkyl; X1 is independently -I, -Br, or Cl; X2 is independently -I, -Br, or -Cl; the group -N(CH2CH2X1)(CH2CH2X2) is independently attached at the 2-position or at the 4-position; each RG is independently -H or an ester substituent; n is independently an integer from 0 to 4; each RP, if present, is independently a phenyl substituent; m is independently an integer from 0 to 4; each RM, if present, is independently a mustard substituent; and pharmaceutically acceptable salts, solvates, amides, and esters thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds; such compounds and compositions for use in methods of treatment of the human or animal body by therapy; the use of such compounds and compositions for the manufacture of medicaments for the treatment of proliferative conditions; and the like.

  本发明涉及一种特定的酶（CPG2）活化的自灭性亚硝基芥子前药，用于酶前药疗法（EPT），如ADEPT和GDEPT，用于治疗增殖性疾病，如癌症，并具有以下结构式：其中RN独立地是C1-7烷基；X1独立地是-I，-Br或Cl；X2独立地是-I，-Br或-Cl；该基团-N(CH2CH2X1)(CH2CH2X2)独立地连接在2位或4位；每个RG独立地是-H或酯基取代物；n独立地是0到4的整数；每个RP（如果存在）独立地是苯基取代物；m独立地是0到4的整数；每个RM（如果存在）独立地是芥子取代物；以及其药学上可接受的盐、溶剂化合物、酰胺和酯。本发明还涉及包含这种化合物的药物组合物；这种化合物和组合物用于通过治疗治疗人体或动物体的方法；这种化合物和组合物用于制造用于治疗增殖性疾病的药物；等等。
• Enzyme activated self-immolative n-substituted nitrogen mustard prodrugs
  申请人：Springer J Caroline

  公开号：US20060069154A1

  公开（公告）日：2006-03-30

  This invention pertains to certain enzyme (CPG2) activated self-immolative nitrogen mustard prodrugs, which are useful in enzyme prodrug therapy (EPT), such as ADEPT and GDEPT, for the treatment of proliferative conditions, such as cancer, and which have the following formula: wherein: R N is independently C 1-7 alkyl; X 1 is independently —I, —Br, or —Cl; X 2 is independently —I, —Br, or —Cl; the group —N(CH 2 CH 2 X 1 )(CH 2 CH 2 X 2 ) is independently attached at the 2-position or at the 4-position; each R G is independently —H or an ester substituent; n is independently an integer from 0 to 4; each R P , if present, is independently a phenyl substituent; m is independently an integer from 0 to 4; each R M , if present, is independently a mustard substituent; and pharmaceutically acceptable salts, solvates, amides, and esters thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds; such compounds and compositions for use in methods of treatment of the human or animal body by therapy; the use of such compounds and compositions for the manufacture of medicaments for the treatment of proliferative conditions; and the like.

  本发明涉及某些酶（CPG2）活化的自我毁灭性亚硝基芥前药，其在酶前药疗法（EPT）如ADEPT和GDEPT中有用，用于治疗增殖性疾病，如癌症，其化学式如下：其中：RN独立地是C1-7烷基；X1独立地是—I，—Br或—Cl；X2独立地是—I，—Br或—Cl；—N(CH2CH2X1)(CH2CH2X2)基团独立地连接在2位或4位；每个RG独立地是—H或酯基取代基；n独立地是0到4的整数；每个RP（如存在）独立地是苯基取代基；m独立地是0到4的整数；每个RM（如存在）独立地是芥子气取代基；以及其药学上可接受的盐，溶剂化合物，酰胺和酯。 本发明还涉及包含这种化合物的制药组合物；这种化合物和组合物用于治疗人体或动物体的治疗方法；使用这种化合物和组合物制造治疗增殖性疾病药物等。
• Process for dyeing, with a lightening effect, human keratin fibers that have been permanently reshaped, using at least one composition comprising at least one fluorescent dye
  申请人：Plos Gregory

  公开号：US20050005368A1

  公开（公告）日：2005-01-13

  A process for dyeing keratin fibers that have previously undergone a permanent reshaping process, comprising applying at least one composition comprising, in a cosmetically acceptable medium, at least one fluorescent dye that is soluble in the medium. The use of the at least one composition may makes it possible to dye a human keratin material, and further, for example, artificially dyed or pigmented hair, with a lightening effect.

  一种用于对先前经过永久性整形过程的角蛋白纤维进行染色的工艺，包括在美容上可接受的介质中涂抹至少一种包含至少一种可溶于介质的荧光染料的组合物。至少一种组合物的使用可以使人类角蛋白材料染色成为可能，例如，还可以使人工染色或颜料染色的头发具有淡化效果。
• Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one compound comprising an acid functional group and processes therefor
  申请人：——

  公开号：US20040256598A1

  公开（公告）日：2004-12-23

  The present disclosure relates to compositions comprising at least one soluble fluorescent dye and at least one compound comprising an acid functional group, and to processes using this composition. It likewise relates to a method of using compositions comprising, in a cosmetically acceptable medium, at least one soluble fluorescent dye and at least one compound comprising an acid functional group for dyeing human keratin materials, such as artificially dyed and/or pigmented hair and dark skin, with a lightening effect.

  本公开涉及包含至少一种可溶性荧光染料和至少一种包含酸官能团的化合物的组合物，以及使用这种组合物的工艺。 同样，它还涉及一种使用组合物的方法，该组合物在美容上可接受的介质中，包含至少一种可溶性荧光染料和至少一种包含酸官能团的化合物，用于对人类角蛋白材料（如人工染色和/或色素头发和深色皮肤）进行染色，以达到美白效果。