6-碘-3H-异苯并呋喃-1-酮 | 53910-10-4

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 中文名称: 6-碘-3H-异苯并呋喃-1-酮
• 中文别名: 6-碘-1(3h)-异苯并呋喃酮
• 英文名称: 6-iodophthalide
• 英文别名: 6-Iodo-3H-isobenzofuran-1-one；6-iodo-3H-2-benzofuran-1-one
• CAS: 53910-10-4
• 化学式: C₈H₅IO₂
• 分子量: 260.031
• InChiKey: GDWUNKJJSAKJSC-UHFFFAOYSA-N

物化性质

• 熔点：
  103 °C
• 沸点：
  382.7±42.0 °C(Predicted)
• 密度：
  2.029±0.06 g/cm3(Predicted)
• 溶解度：
  6.15e-04 M

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932209090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  6-碘-3H-异苯并呋喃-1-酮 在 N-溴代丁二酰亚胺(NBS) 、 sodium methylate 、 potassium hydroxide 、 过氧化苯甲酰 作用下， 以 甲醇 、 四氯化碳 、 氯仿 、 水 、 乙酸乙酯 为溶剂， 反应 37.0h， 生成 (S)-5,6-dihydro-6-(2,3-dihydroxypropyl)-3-iodo-5,11-dioxo-11H-indeno[1,2-c]isoquinoline
  参考文献：
  名称：

  Discovery of Potent Indenoisoquinoline Topoisomerase I Poisons Lacking the 3-Nitro Toxicophore

  摘要：

  3-Nitroindenoisoquinoline human topoisomerase IB (Top1) poisons have potent antiproliferative effects on cancer cells. The undesirable nitro toxicophore could hypothetically be replaced by other functional groups that would retain the desired biological activities and minimize potential safety risks. Eleven series of indenoisoquinolines bearing 3-nitro bioisosteres were synthesized. The molecules were evaluated in the Top1-mediated DNA cleavage assay and in the National Cancer Institute's 60 cell line cytotoxicity assay. The data reveal that fluorine and chlorine may substitute for the 3-nitro group with minimal loss of Top1 poisoning activity. The new information gained from these efforts can be used to design novel indenoisoquinolines with improved safety.

  DOI：

  10.1021/acs.jmedchem.5b00303
• 作为产物：
  描述：

  苯酞 在 盐酸 、 硫酸 、 亚硝酸 、 铁粉 、 potassium nitrate 作用下， 以 水 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 1.17h， 生成 6-碘-3H-异苯并呋喃-1-酮
  参考文献：
  名称：

  呋喃环开环-异香豆素环闭环：2-羧基芳基二呋喃甲烷的再循环反应

  摘要：

  已经开发了合成异香豆素衍生物的通用方法。将双（5-R-2-呋喃基）甲基苯甲酸（R =甲基，乙基）进行环化，然后在甲醇中用氯化氢处理，将其环化为四环异色烯-1-酮衍生物。已经表明，通过改变氢的浓度，可以选择性地获得中间体4-（5-R-呋喃-2-基）-3-（3-氧代-3-R-丙基）-异亚甲基-1-酮。氯化物和反应时间。在R ＝叔丁基的情况下，无论反应如何，仅分离出相应的4- [5-（叔丁基）-2-呋喃基] -3-（4,4-二甲基-3-氧戊基）-1-异壬酮。情况。

  DOI：

  10.1002/jhet.5570430510

文献信息

• [EN] CYCLOHEXYL-AZETIDINYL ANTAGONISTS OF CCR2<br/>[FR] ANTAGONISTES DU CCR2 À BASE DE CYCLOHEXYL-AZÉTIDINYLE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2011159854A1

  公开（公告）日：2011-12-22

  The present invention comprises compounds of Formula (I). Wherein: R1, R2, R4, J, Q, and A are as defined in the specification. The invention also comprises a method of preventing, treating or ameliorating a syndrome, disorder or disease, wherein said syndrome, disorder or disease is type II diabetes, obesity and asthma. The invention also comprises a method of inhibiting CCR2 activity in a mammal by administration of a therapeutically effective amount of at least one compound of Formula (I).

  本发明包括公式(I)的化合物。其中：R1、R2、R4、J、Q和A如说明书所述定义。本发明还包括预防、治疗或改善综合征、障碍或疾病的方法，其中所述综合征、障碍或疾病为2型糖尿病、肥胖和哮喘。本发明还包括通过管理治疗有效量的至少一种公式(I)化合物来抑制哺乳动物中的CCR2活性的方法。
• N-substituted peptidyl nitriles as cysteine cathepsin inhibitors
  申请人：——

  公开号：US20030158256A1

  公开（公告）日：2003-08-21

  Compounds of the formula (I), wherein R 1 is aryl or biaryl; R 2 is aryl-lower alkyl, biaryl-lower alkyl, benzo-fused cycloalkyl, cycloalkyl-lower alkyl, bicycloalkyl-lower alkyl, aryloxy-lower alkyl, or aryl-C 2 -C 7 -alkyl in which C 2 -C 7 -alkyl is interrupted by Y; Y is O, S, SO, SO 2 , CO or NR 6 ; R 3 is hydrogen or lower alkyl; or R 2 and R 3 combined are C 2 -C 7 -alkylene or C 2 -C 7 -alkylene interrupted by Y; R 4 is hydrogen or lower alkyl; R 5 is hydrogen, optionally substituted lower alkyl, aryl-lower alkyl, biaryl-lower alkyl, cycloalkyl-lower alkyl, bicycloalkyl-lower alkyl, aryloxy-lower alkyl, or aryl-C 2 -C 7 -alkyl in which C 2 -C 7 -alkyl is interrupted by Y; R 6 is hydrogen, lower alkyl or aryl-lower alkyl; and pharmaceutically acceptable salts thereof, which are useful as cysteine cathepsin inhibitors.

  式（I）的化合物，其中R1是芳基或联苯基；R2是芳基-较低烷基，联苯基-较低烷基，苯并环烷基，环烷基-较低烷基，双环烷基-较低烷基，芳氧基-较低烷基，或芳基-C2-C7-烷基，其中C2-C7-烷基被Y中断；Y是O，S，SO，SO2，CO或NR6；R3是氢或较低烷基；或R2和R3结合形成C2-C7-烷基或C2-C7-烷基被Y中断；R4是氢或较低烷基；R5是氢，可选择取代的较低烷基，芳基-较低烷基，联苯基-较低烷基，环烷基-较低烷基，双环烷基-较低烷基，芳氧基-较低烷基，或芳基-C2-C7-烷基，其中C2-C7-烷基被Y中断；R6是氢，较低烷基或芳基-较低烷基；及其药学上可接受的盐，可用作半胱氨酸蛋白酶抑制剂。
• Synthesis of 3-Benzylphthalide Derivatives by Using a TDAE Strategy
  作者：Patrice Vanelle、Maroua Ibrahimi、Omar Khoumeri、Raoudha Abderrahim、Thierry Terme

  DOI：10.1055/a-1290-8349

  日期：2021.2

  A one-pot synthesis of new 3-benzylphthalide derivatives was developed by using a strategy based on tetrakis(dimethylamino)ethylene (TDAE). The reactions in the presence of TDAE of substituted benzyl chlorides with methyl 2-formylbenzoate or of substituted methyl-2-formylbenzoates with 4-nitrobenzyl chloride furnished the corresponding isobenzofuran-1(3H)-one products in moderate to good yields.

  使用基于四（二甲氨基）乙烯 (TDAE) 的策略开发了新型 3-苄基苯酞衍生物的一锅法合成。在 TDAE 存在下，取代苄基氯与 2-甲酰基苯甲酸甲酯或取代 2-甲酰基苯甲酸甲酯与 4-硝基苄基氯的反应以中等至良好的产率提供相应的异苯并呋喃-1(3H)-酮产物。
• [EN] N-SUBSTITUTED PEPTIDYL NITRILES AS CYSTEINE CATHEPSIN INHIBITORS<br/>[FR] UTILISATION DE PEPTIDYL NITRILES A SUBSTITUTION- N COMME INHIBITEURS DES CATHEPSINES DE CYSTEINE
  申请人：NOVARTIS AG

  公开号：WO2001087828A1

  公开（公告）日：2001-11-22

  Compounds of the formula (I), wherein R1 is aryl or biaryl; R2 is aryl-lower alkyl, biaryl-lower alkyl, benzo-fused cycloalkyl, cycloalkyl-lower alkyl, bicycloalkyl-lower alkyl, aryloxy-lower alkyl, or aryl-C2-C7-alkyl in which C2-C7-alkyl is interrupted by Y; Y is O, S, SO, SO2, CO or NR6; R3 is hydrogen or lower alkyl; or R2 and R3 combined are C2-C7-alkylene or C2-C7-alkylene interrupted by Y; R4 is hydrogen or lower alkyl; R5 is hydrogen, optionally substituted lower alkyl, aryl-lower alkyl, biaryl-lower alkyl, cycloalkyl-lower alkyl, bicycloalkyl-lower alkyl, aryloxy-lower alkyl, or aryl-C2-C7-alkyl in which C2-C7-alkyl is interrupted by Y; R6 is hydrogen, lower alkyl or aryl-lower alkyl; and pharmaceutically acceptable salts thereof, which are useful as cysteine cathepsin inhibitors.

  该式化合物（I）的化合物，其中R1是芳基或双芳基；R2是芳基-较低烷基，双芳基-较低烷基，苯并环烷基，环烷基-较低烷基，双环烷基-较低烷基，芳氧基-较低烷基，或芳基-C2-C7-烷基，其中C2-C7-烷基被Y中断；Y是O，S，SO，SO2，CO或NR6；R3是氢或较低烷基；或R2和R3结合是C2-C7-亚烷基或C2-C7-亚烷基，其中被Y中断；R4是氢或较低烷基；R5是氢，可选择性取代的较低烷基，芳基-较低烷基，双芳基-较低烷基，环烷基-较低烷基，双环烷基-较低烷基，芳氧基-较低烷基，或芳基-C2-C7-烷基，其中C2-C7-烷基被Y中断；R6是氢，较低烷基或芳基-较低烷基；以及其药学上可接受的盐，它们可用作半胱氨酸蛋白酶抑制剂。
• Anti-inflammatory phthalazinones
  申请人：Pennwalt Corporation

  公开号：US04665181A1

  公开（公告）日：1987-05-12

  A compound useful as anti-inflammatory agents in warm-blooded animals of the formula ##STR1## wherein X is a member of the class of ethylene and ethenyl and is substituted for hydrogen in the sixth or seventh position of the 1(2H)-phthalazinone ring Y is a member of the class of hydrogen and hydroxyl R.sub.1 is a member of the class of hydrogen, alkyl, alkoxy, hydroxyl, halogen, nitro, --NR.sub.3 R.sub.4, --COR.sub.5 and --O--A wherein A is a mineral acid residue which with --O-- forms an ester or the alkali metal salt of said ester, R.sub.2 is a member of the class of hydrogen, alkyl, phenyl, substituted phenyl, heteroaryl, hydroxyalkylene, polyhydroxyalkylene, aminoalkylene, alkylaminoalkylene, and carboxyalkylene, R.sub.3, R.sub.4 are independently from the class of hydrogen, alkyl, aminoalkylene or alkylaminoalkylene, R.sub.5 is a member of the class of OR.sub.3 and ##STR2## for example hydroxyl, methoxyl, 2-dimethylaminoethoxyl or 2-dimethylaminoethylamino, and wherein by alkyl and alkylene is meant respectively a mono- or divalent saturated aliphatic radical containing up to about eight carbon atoms, wherein the nitrogen of the alkylamino or alkylaminoalkylene may form a heterocycle with the alkyl or alkylene groups, wherein substituted phenyl may be substituted by, for example, alkyl, hydroxyl, alkoxy, halogen, nitro or amino, wherein heteroaryl may be, for example, 2-pyridyl.

  该化合物适用于温血动物的抗炎药，其化学式为##STR1##其中X是乙烯和乙烯基类的成员，并在1（2H）-邻苯二酮环的第六或第七位置上替代氢，Y是氢和羟基类的成员，R.sub.1是氢，烷基，烷氧基，羟基，卤素，硝基，--NR.sub.3 R.sub.4，--COR.sub.5和--O--A类的成员，其中A是矿物酸残基，与--O--形成酯或所述酯的碱金属盐，R.sub.2是氢，烷基，苯基，取代苯基，杂环芳基，羟基烷基，多羟基烷基，氨基烷基，烷基氨基烷基和羧基烷基类的成员，R.sub.3，R.sub.4是独立地来自氢，烷基，氨基烷基或烷基氨基烷基类，R.sub.5是OR.sub.3和##STR2##类的成员，例如羟基，甲氧基，2-二甲基氨基乙氧基或2-二甲基氨基乙基氨基，其中烷基和烷基烯是指分别包含多达约八个碳原子的单价或二价饱和脂肪基，其中烷基氨基或烷基氨基烷基的氮原子可以与烷基或烷基烯基形成杂环，其中取代苯基可以被烷基，羟基，烷氧基，卤素，硝基或氨基取代，其中杂环芳基可以是例如2-吡啶基。