4-Chlor-2-nitro-zimtsaeure | 20357-27-1

• 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: 4-Chlor-2-nitro-zimtsaeure
• 英文别名: 4-Chlor-o-nitro-zimtsaeure；4-chloro-2-nitro-cinnamic acid；β-(4-Chlor-2-nitro-phenyl)-acrylsaeure；3-(4-Chloro-2-nitrophenyl)prop-2-enoic acid
• CAS: 20357-27-1
• 化学式: C₉H₆ClNO₄
• 分子量: 227.604
• InChiKey: UFPCDBZSIBYWIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 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：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Chlor-2-nitro-zimtsaeure 在 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 18.33h， 生成 (E)-N-Benzyl-3-(4-chloro-2-isocyanato-phenyl)-acrylamide
  参考文献：
  名称：

  Carling; Leeson; Moore, Journal of Medicinal Chemistry, 1993, vol. 36, # 22, p. 3397 - 3408

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Nitro-4-chlorbenzaldoxim 在 iron (III)-ammonium sulfate 、 硫酸 、 sodium acetate 作用下， 生成 4-Chlor-2-nitro-zimtsaeure
  参考文献：
  名称：

  Functional hyperandrogenism detected by corticotropin and GnRH-analogue stimulation tests in women affected by apparently idiopathic hirsutism

  摘要：

  The etiologic diagnosis of hirsutism is often difficult. Previous studies have reported normal basal androgen and SHBG concentrations in 33-50% of hirsute women, suggesting the presence of an "idiopathic" form of hirsutism as the most frequent cause of this problem. The recent use of GnRH-analogues together with the corticotropin stimulation test allows better understanding of whether the cause of hirsutism is androgen excess and, if so, whether the origin of the latter is ovarian, adrenal or both. The present study evaluated adrenal and ovarian function in 48 young hirsute women as well as in 78 normal women matched for body mass index and age, who acted as control group. To determine ovarian function, a single 100-mug dose of GnRH analogue triptorelin was injected sc; thereafter, gonadotropins, 17-hydroxyprogesterone (17-OHP), Delta4-androstenedione (Delta4), total testosterone (T) and estradiol were determined. To better understand the adrenal function, 250 mug of 1,24 ACTH were administrated as iv infusion for 5 h, and plasma cortisol (F), 17-OHP, Delta4, DHEAS, T, 11-desossicortisol were measured. The combined use of these two stimulation tests was able to detect mild to moderate abnormalities in the steroidogenesis of ovaries alone (23%), adrenals alone (16.6%), or both (35.4%) in most hirsute women (75%) with otherwise normal baseline androgen concentrations. In particular, patients showed significantly increased responses of 17-OHP, Delta4, total T, 11-desossicortisol, and F to 1,24-ACTH administration. Moreover, they also had significantly higher 17-OHP and T responses to triptorelin. In conclusion, milder forms of functional ovarian and/or adrenal hyperandrogenism, similar to those found in clearly hyperandrogenic women, were observed and could be an underlying mechanism of idiopathic hirsutism. (J. Endocrinol. Invest. 24: 491-498, 2001) (C) 2001, Editrice Kurtis.

  DOI：

  10.1007/bf03343881

文献信息

• Heteroaryl piperazine antipsychotic agents
  申请人：Pfizer Inc

  公开号：US05350747A1

  公开（公告）日：1994-09-27

  Compounds of the formula ##STR1## and pharmaceutical compositions comprising them, wherein R.sup.1, Z, X, W and Y are as defined below. The compounds are useful in the treatment of psychosis and anxiety.

  公式##STR1##的化合物和包含它们的药物组合物，其中R.sup.1，Z，X，W和Y如下定义。这些化合物可用于治疗精神疾病和焦虑症。
• [EN] MACROCYCLIC QUINAZOLINE DERIVATIVES AS ANTIPROLIFERATIVE AGENTS<br/>[FR] DERIVES DE QUINAZOLINE MACROCYCLIQUE UTILISES COMME AGENTS ANTIPROLIFERATIFS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2004105765A1

  公开（公告）日：2004-12-09

  The present invention concerns the compounds of formula (I) the N-oxide forms, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein Z represents O, CH2, NH or S; in particular Z represents NH; Y represents -C3-9alkyl-, -C3-9alkenyl-, -C3-9alkynyl-, -C3-7alkyl-CO-NH- optionally substituted with amino, mono- or di(C1-4alkyl)amino or C1-4 alkyloxycarbonylamino-, -C3-7alkenyl-CO-NH- optionally substituted with amino, mono- or di(C1-4alkyl)amino- or C1-4alkyloxycarbonylamino-, C1-5alkyl-oxy-C1-5alkyl-, -C1-5alkyl NR13-, -C1-5alkyl-, -C1-5alkyl-NR14-CO-C1-5alkyl-, -C1-5alkyl-CO NR15-C1-5alkyl-, -C1-6alkyl-CO-NH-, -C1-6alkyl-NH-CO-, -C1-3alkyl-NH-CS-Het20-, -C1-3alkyl-NH-CO-Het20-, -C1-2alkyl-CO-Het21-CO-, -Het22-CH2-CO-NH-C1-3alkyl-, -CO-NH-C1-6alkyl-, -NH-CO-C1-6alkyl-, -CO-C1-7alkyl-, -C1-7alkyl-CO-, -C1-6alkyl-CO-C1-6alkyl-, -C1-2alkyl-NH-CO-CR16R17-NH-, -C1-2alkyl-CO-NH-CR18R19-CO-, -C1-2alkyl-CO-NR20-C1-3alkyl-CO-, C1-2alkyl-NR21-CH2-CO-NH-C1-3alkyl-, or -NR22-CO-C1-3alkyl-NH-; X1 represents a direct bond, O or -O-C1-2alkyl-, CO, -CO-C1-2alkyl-, NR11, -NR11-C1-2alkyl-, CH2-, -O-N=CH- or -C1-2alkyl-; X2 represents a direct bond, O, -O-C1-2alkyl-, CO, -CO-C1-2alkyl-, NR12, -NR12-C1-2alkyl-, -CH2-, -O-N=CH- or -C1-2alkyl-. The growth inhibitory effect anti-tumour activity of the present compounds has been demonstrated in vitro, in enzymatic assays on the receptor tyrosine kinase EGFR.

  本发明涉及公式（I）的化合物，其N-氧化物形式，药用可接受的加合物盐及其立体化异构形式，其中Z代表O、CH2、NH或S；特别是Z代表NH；Y代表-C3-9烷基，-C3-9烯基，-C3-9炔基，-C3-7烷基-CO-NH-（可选择地被氨基，单或双（C1-4烷基）氨基或C1-4烷氧羰氨基取代），-C3-7烯基-CO-NH-（可选择地被氨基，单或双（C1-4烷基）氨基或C1-4烷氧羰氨基取代），C1-5烷氧基-C1-5烷基，-C1-5烷基-NR13-，-C1-5烷基，-C1-5烷基-NR14-CO-C1-5烷基，-C1-5烷基-CO NR15-C1-5烷基，-C1-6烷基-CO-NH-，-C1-6烷基-NH-CO-，-C1-3烷基-NH-CS-Het20-，-C1-3烷基-NH-CO-Het20-，-C1-2烷基-CO-Het21-CO-，-Het22-CH2-CO-NH-C1-3烷基-，-CO-NH-C1-6烷基-，-NH-CO-C1-6烷基-，-CO-C1-7烷基-，-C1-7烷基-CO-，-C1-6烷基-CO-C1-6烷基-，-C1-2烷基-NH-CO-CR16R17-NH-，-C1-2烷基-CO-NH-CR18R19-CO-，-C1-2烷基-CO-NR20-C1-3烷基-CO-，C1-2烷基-NR21-CH2-CO-NH-C1-3烷基-，或-NR22-CO-C1-3烷基-NH-；X1代表直接键，O或-O-C1-2烷基-，CO，-CO-C1-2烷基-，NR11，-NR11-C1-2烷基-，CH2-，-O-N=CH-或-C1-2烷基-；X2代表直接键，O，-O-C1-2烷基-，CO，-CO-C1-2烷基-，NR12，-NR12-C1-2烷基-，-CH2-，-O-N=CH-或-C1-2烷基-。本发明化合物的生长抑制效应和抗肿瘤活性已在体外实验中，在EGFR受体酪氨酸激酶的酶促活性测定中得到证明。
• Anti-inflammatory properties of a series of phenyl- and phenoxy-alkanoic acids
  作者：D J Drain、M J Daly、B Davy、M Horlington、J G B Howes、J M Scruton、R A Selway

  DOI：10.1111/j.2042-7158.1970.tb12754.x

  日期：2012.1.25

  Some o-benzamidophenoxyacetic, phenylalkanoic and phenoxyalkanoic acids have been synthesized. Anti-inflammatory activity was measured by the phenylbenzoquinone writhing test in mice and the rat foot oedema test. Meta- and para-substitutions in the benzamido-ring, promoting lipid solubility, enhanced the potency, whereas substitution with polar groups reduced it. Further phenylring substitution in the 2-(3,4-dichlorobenzamido)phenoxyacetic acids only slightly affected the potency. Side-chain modifications did not increase the activity on the three substituted phenoxyacetic acids chosen. Two phenylpropionic acids showed a good order of activity but the respective cinnamic acids were virtually inactive. From the investigations 2-(3,4-dichlorobenzamido)phenoxyacetic acid (SNR. 1804) was selected for further studies is now undergoing clinical evaluation.

  摘要：已合成一些o-苯甲酰基苯氧乙酸、苯基烷酸和苯氧烷酸。通过小鼠苯基苯醌扭曲实验和大鼠足部水肿实验测量了抗炎活性。苯甲酰环中的间位和对位取代，促进了脂溶性，增强了效力，而用极性基团取代则降低了效力。在2-(3,4-二氯苯甲酰胺)苯氧乙酸中进一步取代苯环仅稍微影响了效力。侧链修饰并未增加所选的三种取代苯氧乙酸的活性。两种苯丙酸显示出良好的活性顺序，但相应的肉桂酸几乎无活性。从研究中选择了2-(3,4-二氯苯甲酰胺)苯氧乙酸（SNR. 1804）进行进一步研究，目前正在进行临床评估。
• Functional hyperandrogenism detected by corticotropin and GnRH-analogue stimulation tests in women affected by apparently idiopathic hirsutism
  作者：Riccardo Rossi、L. Tauchmanovà、A. Luciano、R. Valentino、S. Savastano、C. Battista、M. Di Martino、G. Lombardi

  DOI：10.1007/bf03343881

  日期：2001.7

  The etiologic diagnosis of hirsutism is often difficult. Previous studies have reported normal basal androgen and SHBG concentrations in 33-50% of hirsute women, suggesting the presence of an "idiopathic" form of hirsutism as the most frequent cause of this problem. The recent use of GnRH-analogues together with the corticotropin stimulation test allows better understanding of whether the cause of hirsutism is androgen excess and, if so, whether the origin of the latter is ovarian, adrenal or both. The present study evaluated adrenal and ovarian function in 48 young hirsute women as well as in 78 normal women matched for body mass index and age, who acted as control group. To determine ovarian function, a single 100-mug dose of GnRH analogue triptorelin was injected sc; thereafter, gonadotropins, 17-hydroxyprogesterone (17-OHP), Delta4-androstenedione (Delta4), total testosterone (T) and estradiol were determined. To better understand the adrenal function, 250 mug of 1,24 ACTH were administrated as iv infusion for 5 h, and plasma cortisol (F), 17-OHP, Delta4, DHEAS, T, 11-desossicortisol were measured. The combined use of these two stimulation tests was able to detect mild to moderate abnormalities in the steroidogenesis of ovaries alone (23%), adrenals alone (16.6%), or both (35.4%) in most hirsute women (75%) with otherwise normal baseline androgen concentrations. In particular, patients showed significantly increased responses of 17-OHP, Delta4, total T, 11-desossicortisol, and F to 1,24-ACTH administration. Moreover, they also had significantly higher 17-OHP and T responses to triptorelin. In conclusion, milder forms of functional ovarian and/or adrenal hyperandrogenism, similar to those found in clearly hyperandrogenic women, were observed and could be an underlying mechanism of idiopathic hirsutism. (J. Endocrinol. Invest. 24: 491-498, 2001) (C) 2001, Editrice Kurtis.
• Carling; Leeson; Moore, Journal of Medicinal Chemistry, 1993, vol. 36, # 22, p. 3397 - 3408
  作者：Carling、Leeson、Moore、Smith、Moyes、Mawer、Thomas、Chan、Baker、Foster、et al.

  DOI：——

  日期：——