Acetic acid 4-nitrooxymethyl-phenyl ester | 91735-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: Acetic acid 4-nitrooxymethyl-phenyl ester
• 英文别名: [4-(nitrooxymethyl)phenyl] acetate
• CAS: 91735-04-5
• 化学式: C₉H₉NO₅
• 分子量: 211.174
• InChiKey: NOHPDJDDUIXDPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-乙酰氧基苯甲醛 在 吡啶 、 sodium tetrahydroborate 、 氯化亚砜 、 silver nitrate 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 4.0h， 生成 Acetic acid 4-nitrooxymethyl-phenyl ester
  参考文献：
  名称：

  Chemical Insights in the Concept of Hybrid Drugs:  The Antitumor Effect of Nitric Oxide-Donating Aspirin Involves A Quinone Methide but Not Nitric Oxide nor Aspirin

  摘要：

  Hybrid drug 1 (NO-ASA) continues to attract intense research from chemists and biologists alike. It consists of ASA and a -ONO2 group connected through a spacer and is in preclinical development as an antitumor drug. We report that, contrary to current beliefs, neither ASA nor NO contributes to this antitumor effect. Rather, an unsubstituted QM was identified as the sole cytotoxic agent. QM forms from 1 after carboxylic ester hydrolysis and, in accordance with the HSAB theory, selectively reacts with cellular GSH, which in turn triggers cell death. Remarkably, a derivative lacking ASA and the -ONO2 group is 10 times more effective than 1. Thus, our data provide a conclusive molecular mechanism for the antitumor activity of 1. Equally importantly, we show for the first time that a "presumed invisible" linker in a hybrid drug is not so invisible after all and is in fact solely responsible for the biological effect.

  DOI：

  10.1021/jm061371e

文献信息

• [EN] COMPOUNDS USEFUL IN THE TREATMENT OF NEOPLASTIC DISEASES<br/>[FR] COMPOSÉS UTILES DANS LE TRAITEMENT DE MALADIES NÉOPLASIQUES
  申请人：UNIVERSITÄT ZU KÖLN

  公开号：WO2015044177A1

  公开（公告）日：2015-04-02

  The present invention refers to compounds of formula: (formula A), wherein R1 is selected from (formula I), (formula II), (formula (III), (formula IV), (formula V), or (formula B), and wherein R2, R3, R4 and R5 are as defined in the claims and X is OTBS, hydroxy, formyloxy, acetoxy, nitrooxy, nitrooxymethyl, or a halogen; and pharmaceutically acceptable salts thereof, which are useful in the treatment of neoplastic or proliferative disorders, a pharmaceutical composition comprising such a compound and a method preparing this compound.

  本发明涉及以下式的化合物：（式A），其中R1从（式I），（式II），（式III），（式IV），（式V）或（式B）中选择，并且其中R2，R3，R4和R5如权利要求中定义的那样，X为OTBS，羟基，甲酰氧基，乙酰氧基，硝基氧基，硝基甲氧基或卤素；及其药学上可接受的盐，用于治疗肿瘤性或增生性疾病，包括这种化合物的药物组合物和制备该化合物的方法。
• Photochemical nitrooxylation of methylbenzenes by cerium(IV) ammonium nitrate in acetonitrile
  作者：E. Baciocchi、C. Rol、G.V. Sebastiani、B. Serena

  DOI：10.1016/s0040-4039(01)90082-6

  日期：1984.1

  The photochemical reaction of substituted toluenes with CAN in CH3CN leads to good yields of benzyl nitrates under very mild conditions.

  在非常温和的条件下，取代的甲苯与CAN在CH 3 CN中的光化学反应导致硝酸苄基酯的良好收率。
• Compounds useful in the treatment of neoplastic diseases
  申请人：UNIVERSITÄT ZU KÖLN

  公开号：US10793509B2

  公开（公告）日：2020-10-06

  Compounds and pharmaceutically acceptable salts of the compounds are useful in the treatment of neoplastic diseases or proliferative disorders. The compounds are formulated into pharmaceutical compositions, which can be used in methods of treating neoplastic diseases or proliferative disorders The compounds are useful to treat cancers such as prostate, pancreatic, lung, skin, breast, bladder, colon, and blood cancers. The compounds are represented by the following formula:

  化合物及其药学上可接受的盐类可用于治疗肿瘤性疾病或增殖性疾病。 这些化合物可配制成药物组合物，用于治疗肿瘤性疾病或增殖性疾病。 这些化合物用下式表示：
• BACIOCCHI, E.;ROL, C.;SEBASTIANI, G. V.;SERENA, B., TETRAHEDRON LETT., 1984, 25, N 18, 1945-1946
  作者：BACIOCCHI, E.、ROL, C.、SEBASTIANI, G. V.、SERENA, B.

  DOI：——

  日期：——
• COMPOUNDS USEFUL IN THE TREATMENT OF NEOPLASTIC DISEASES
  申请人：Universität zu Köln

  公开号：EP3049386A1

  公开（公告）日：2016-08-03