2-hydroxycinnamoyl chloride | 868163-16-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-hydroxycinnamoyl chloride
• 英文别名: (E)-3-(2-hydroxyphenyl)prop-2-enoyl chloride
• CAS: 868163-16-0
• 化学式: C₉H₇ClO₂
• 分子量: 182.606
• InChiKey: GKQNEFDXLRMEPM-AATRIKPKSA-N

物化性质

• 沸点：
  317.4±17.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxycinnamoyl chloride 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 氯仿 为溶剂， 反应 0.5h， 生成 (E)-N-hydroxy-3-(2-hydroxyphenyl)acrylamide
  参考文献：
  名称：

  Synthesis and biological evaluation of cinnamyl compounds as potent antitumor agents

  摘要：

  A series of cinnamyl compounds related to 2'-hydroxycinnamaldehyde were synthesized and their antitumor effects against human cancer cells evaluated. Hydroxylamine derivative 6 inhibited the growth of human cancer cells and human colon tumor xenograft in nude mice. Its antitumor effects belong to the induction of apoptosis and arresting cell cycle at G(2)/M phase, which is confirmed by detection of apoptosis markers and cell cycle analysis. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.033
• 作为产物：
  描述：

  反式-2-羟基肉桂酸 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-hydroxycinnamoyl chloride
  参考文献：
  名称：

  新的潜在多巴胺D3受体放射性配体（E）-4,3,2- [11C]甲氧基-N-4-（4-（2-甲氧基苯基）哌嗪-1-基）丁基-肉桂酰胺的合成及初步PET成像。

  摘要：

  D3受体放射性配体（E）-4,3,2- [11C]甲氧基-N-4-（4-（2-甲氧基苯基）哌嗪-1-基）丁基肉桂酰胺（4- [11C] MMC，[11C合成了] 1a; 3- [11C] MMC，[11C] 1b;和2- [11C] MMC，[11C] 1c）作为脑D3受体的新型潜在正电子发射断层扫描（PET）成像剂进行评估。通过对相应的前体（E）-4,3,2-羟基-N-4-（4-（2-甲氧基苯基）哌嗪）进行O- [11C]甲基化来制备新的示踪剂4,3,2- [11C] MMC使用[11C]三氟甲磺酸甲酯，通过固相萃取（SPE）纯化程序分离出-1-基）丁基肉桂酰胺（4,3,2-HMCs），放射化学产率为40-65％，衰变校正至轰击结束（EOB），合成时间为15-20分钟。使用我们实验室开发的动物PET扫描仪IndyPET-II对大鼠中的示踪剂[11C] 1a-c进行PET动力学研究。结果显示，脑摄取序列为4-

  DOI：

  10.1016/j.bmc.2005.06.055

文献信息

• Studies on a Novel, Potent and Orally Effective Cholecystokinin A Antagonist, FK-480. Synthesis and Structure-Activity Relationships of FK-480 and Related Compounds.
  作者：Yoshinari SATOH、Teruaki MATSUO、Hajime SOGABE、Harunobu ITOH、Toshiji TADA、Takayoshi KINOSHITA、Keizou YOSHIDA、Takao TAKAYA

  DOI：10.1248/cpb.42.2071

  日期：——

  We prepared various novel tricyclic 1, 4-benzodiazepine derivatives as cholecystokinin (CCK) A antagonists, which were evaluated preliminarily for inhibition of <125>I-CCK-8 binding to rat pancreatic membranes in vitro and inhibiting effect on CCK-8-induced inhibition of charcoal meal gastric emptying in mice. On the basis of structure-activity relationship (SAR) studies, as well as the stability and availability of the starting materials of those compounds, (S)-N-[1-(2-fluorophenyl)-3, 4, 6, 7-tetrahydro-4-oxo-pyrrolo[3, 2, 1-jk][1, 4]benzodiazepin-3-yl]-1H-indole-2-carboxamide (9f, FK-480) was selected as a candidate compound for further evaluation. The absolute configuration of the precursor of FK-480, (3S)-amino-1, 4-benzodiazepine derivative ((S)-8a, R1=F) was determined by an X-ray crystallographic study of its ureido derivative with (S)-α-methylbenzyl isocyanate.FK-480 is now undergoing clinical studies for the treatment of chronic pancreatitis.

  我们制备了多种新型三环1,4-苯并二氮杂䓬衍生物作为胆囊收缩素（CCK）A受体拮抗剂，并初步评估了它们对<125>I-CCK-8与大鼠胰腺膜体外结合的抑制作用以及对CCK-8诱导的小鼠活性炭餐胃排空的抑制作用。基于构效关系（SAR）研究以及这些化合物的起始原料的稳定性和可获得性，我们选择了(S)-N-[1-(2-氟苯基)-3,4,6,7-四氢-4-氧代-吡咯并[3,2,1-jk][1,4]苯并二氮杂䓬-3-基]-1H-吲哚-2-甲酰胺（9f, FK-480）作为候选化合物进行进一步评估。通过与(S)-α-甲基苄基异氰酸酯的脲基衍生物的X射线晶体学研究，确定了FK-480前体(3S)-氨基-1,4-苯并二氮杂䓬衍生物（(S)-8a, R1=F）的绝对构型。FK-480目前正在进行治疗慢性胰腺炎的临床研究。
• Azonafide derivatives, methods for their production and pharmaceutical compositions therefrom
  申请人：Unibioscreen S.A.

  公开号：EP1787985A1

  公开（公告）日：2007-05-23

  Azonafide derivatives are obtained by reacting azonafide with aldehydes, acyl halides, thioacyl halides, monoisocyanates, isothiocyanates or polyamines, and are useful as active ingredients of pharmaceutical compositions for the treament of cell proliferative disorders.

  Azonafide衍生物是通过将azonafide与醛类、酰卤、硫酰卤、单异氰酸酯、异硫氰酸酯或多胺反应而得到的，它们可作为药物组合物的有效成分，用于治疗细胞增殖性疾病。
• Azonafide Derivatives, Methods for Their Production and Pharmaceutical Compositions Therefrom
  申请人：Van Quaquebeke Eric

  公开号：US20080292585A1

  公开（公告）日：2008-11-27

  Azonafide derivatives are obtained by reacting azonafide with aldehydes, acyl halides, thioacyl halides, monoisocyanates, isothiocyanates, sulfonyl halides, monohalogenoalkanes, monohalogenoalkenes or monohalogenoalkynes, and are useful as active ingredients of pharmaceutical compositions for the prevention and treatment of cell proliferative disorders, in particular several forms of Cancer.

  Azonafide衍生物是通过将azonafide与醛类、酰卤、硫酰卤、单异氰酸酯、异硫氰酸酯、磺酰卤、单卤代烷烃、单卤代烯烃或单卤代炔烃反应得到的，并且它们可用作制药组合物的活性成分，用于预防和治疗细胞增殖性疾病，特别是几种癌症。
• US7741337B2
  申请人：——

  公开号：US7741337B2

  公开（公告）日：2010-06-22
• Synthesis and biological evaluation of cinnamyl compounds as potent antitumor agents
  作者：Dae-Seop Shin、Jiin Kim、Dong Cho Han、Kwang-Hee Son、Chang Woo Lee、Hwan-Mook Kim、Su Hyung Hong、Byoung-Mog Kwon

  DOI：10.1016/j.bmcl.2007.07.033

  日期：2007.10

  A series of cinnamyl compounds related to 2'-hydroxycinnamaldehyde were synthesized and their antitumor effects against human cancer cells evaluated. Hydroxylamine derivative 6 inhibited the growth of human cancer cells and human colon tumor xenograft in nude mice. Its antitumor effects belong to the induction of apoptosis and arresting cell cycle at G(2)/M phase, which is confirmed by detection of apoptosis markers and cell cycle analysis. (C) 2007 Elsevier Ltd. All rights reserved.