(E)-3-(2-Chloro-5-nitro-phenyl)-acrylic acid ethyl ester | 111126-07-9

• 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: (E)-3-(2-Chloro-5-nitro-phenyl)-acrylic acid ethyl ester
• 英文别名: Ethyl 2-chloro-5-nitrocinnamate；ethyl 3-(2-chloro-5-nitrophenyl)prop-2-enoate
• CAS: 111126-07-9
• 化学式: C₁₁H₁₀ClNO₄
• 分子量: 255.658
• InChiKey: NDPKHIUCDBOBGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  376.1±32.0 °C(Predicted)
• 密度：
  1.340±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-Chloro-5-nitro-phenyl)-acrylic acid ethyl ester 在 铁粉 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 ethyl 5-amino-2-chlorocinnamate
  参考文献：
  名称：

  GDC-0449—A potent inhibitor of the hedgehog pathway

  摘要：

  SAR for a wide variety of heterocyclic replacements for a benzimidazole led to the discovery of functionalized 2-pyridyl amides as novel inhibitors of the hedgehog pathway. The 2-pyridyl amides were optimized for potency, PK, and drug-like properties by modifications to the amide portion of the molecule resulting in 31 (GDC-0449). Amide 31 produced complete tumor regression at doses as low as 12.5 mg/kg BID in a medulloblastoma allograft mouse model that is wholly dependent on the Hh pathway for growth and is currently in human clinical trials, where it is initially being evaluated for the treatment of BCC. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.049
• 作为产物：
  描述：

  2-氯-5-硝基苯甲醛 、 乙氧甲酰基亚甲基三苯基膦 以 甲苯 为溶剂， 生成 (E)-3-(2-Chloro-5-nitro-phenyl)-acrylic acid ethyl ester
  参考文献：
  名称：

  GDC-0449—A potent inhibitor of the hedgehog pathway

  摘要：

  SAR for a wide variety of heterocyclic replacements for a benzimidazole led to the discovery of functionalized 2-pyridyl amides as novel inhibitors of the hedgehog pathway. The 2-pyridyl amides were optimized for potency, PK, and drug-like properties by modifications to the amide portion of the molecule resulting in 31 (GDC-0449). Amide 31 produced complete tumor regression at doses as low as 12.5 mg/kg BID in a medulloblastoma allograft mouse model that is wholly dependent on the Hh pathway for growth and is currently in human clinical trials, where it is initially being evaluated for the treatment of BCC. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.049

文献信息

• Nitro or amino substituted phenylalkyl or phenylalkenyl carboxylic acid
  申请人：BASF Aktiengesellschaft

  公开号：US05237089A1

  公开（公告）日：1993-08-17

  N-substituted 3,4,5,6-tetrahydrophthalimides and their intermediates of the general formula I ##STR1## where A is --NO.sub.2, --NH.sub.2 or ##STR2## corresponding to the compounds Ia, Ib and Ic, B is --CH.sub.2 --, --CH.sub.2 --CHR.sup.1 --, --CH.sub.2 --CHR.sup.1 --CH.sub.2 --, --CH.dbd., --CH.dbd.CR.sup.1 -- or --CH.dbd.CR.sup.1 --CH.dbd., R.sup.1 being --H, --Cl, --Br or --CH.sub.3, D is ##STR3## or .dbd.C<, depending on the terminal group B, X is --H, --Cl or --Br, Y is --H, C.sub.1 -C.sub.7 -alkyl, --Cl, --Br, --CN, --CONH.sub.2 or --CO.sub.2 R.sup.2, where R.sup.2 is H, C.sub.1 -C.sub.6 -alkyl, C.sub.5 - or C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylmercapto-C.sub.2 -C.sub.4 -alkyl, propargyl, benzyl, .alpha.-phenylethyl, .alpha.-phenylpropyl, C.sub.2 -C.sub.4 -alkyl which is monosubstituted, disubstituted or trisubstituted by F or Cl, or CH.sub.3 -substituted or Cl-substituted allyl, and Z is --COOR.sup.2, --CONR.sup.3 R.sup.4, ##STR4## or --COR.sup.2, where R.sup.3 and R.sup.4 are each H or C.sub.1 -C.sub.4 -alkyl or together form a 5-membered or 6-membered cycloaliphatic ring whose carbon chain may be interrupted by an oxygen atom.

  一般式I的N取代的3,4,5,6-四氢酞酰亚胺及其中间体，其中A是--NO.sub.2，--NH.sub.2或##STR2##相应于化合物Ia，Ib和Ic，B是--CH.sub.2--，--CH.sub.2--CHR.sup.1--，--CH.sub.2--CHR.sup.1--CH.sub.2--，--CH.dbd.，--CH.dbd.CR.sup.1--或--CH.dbd.CR.sup.1--CH.dbd.，其中R.sup.1是--H，--Cl，--Br或--CH.sub.3，D是##STR3##或.dbd.C<，取决于末端基团B，X是--H，--Cl或--Br，Y是--H，C.sub.1-C.sub.7-烷基，--Cl，--Br，--CN，--CONH.sub.2或--CO.sub.2R.sup.2，其中R.sup.2是H，C.sub.1-C.sub.6-烷基，C.sub.5-或C.sub.6-环烷基，C.sub.1-C.sub.4-烷氧基-C.sub.2-C.sub.4-烷基，C.sub.1-C.sub.4-烷基硫醇-C.sub.2-C.sub.4-烷基，丙炔基，苄基，.alpha.-苯乙基，.alpha.-苯丙基，C.sub.2-C.sub.4-烷基，其被F或Cl单取代，双取代或三取代，或CH.sub.3-取代或Cl-取代的烯丙基，Z是--COOR.sup.2，--CONR.sup.3R.sup.4，##STR4##或--COR.sup.2，其中R.sup.3和R.sup.4各自是H或C.sub.1-C.sub.4-烷基，或共同形成一个5-成员或6-成员的环状脂肪环，其碳链可以被氧原子中断。
• N-substituted 3,4,5,6-tetrahydrophthalimides and their intermediates
  申请人：BASF Aktiengesellschaft

  公开号：US05062884A1

  公开（公告）日：1991-11-05

  N-substituted 3,4,5,6-tetrahydrophthalimides and their intermediates of the general formula I ##STR1## where A is --NO.sub.2, --NH.sub.2 or ##STR2## corresponding to the compounds Ia, Ib and Ic, B is --CH.sub.2 --, --CH.sub.2 --CHR.sup.1 --, --CH.sub.2 --CHR.sup.1 --CH.sub.2 --, --CH.dbd., --CH.dbd.CR.sup.1 -- or --CH.dbd.CR.sup.1 --CH.dbd., R.sup.1 being --H, --Cl, --Br or --CH.sub.3, D is ##STR3## depending on the terminal group B, X is --H, --Cl or --Br, Y is --H, C.sub.1 -C.sub.7 --alkyl, --Cl, --Br, --CN, --CONH.sub.2 --CO.sub.2 R.sup.2, where R.sup.2 is H, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -- or C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylmercapto-C.sub.2 -C.sub.4 -alkyl, propargyl, benzyl, .alpha.-phenylethyl, .alpha.-phenylpropyl, C.sub.2 -C.sub.4 -alkyl which is monosubstituted, disubstituted or trisubstituted by F or Cl, or CH.sub.3 -substituted or Cl-substituted allyl, and Z is --COOR.sup.2, --CONR.sup.3 R.sup.4, ##STR4## where R.sup.3 and R.sup.4 are each H or C.sub.1 -C.sub.4 -alkyl or together form a 5-membered or 6-membered cycloaliphatic ring whose carbon chain may be interrupted by an oxygen atom.

  一般式I的N-取代的3,4,5,6-四氢酞酰亚胺及其中间体 ##STR1## 其中A为--NO.sub.2，--NH.sub.2或##STR2## 对应于化合物Ia，Ib和Ic，B为--CH.sub.2--，--CH.sub.2--CHR.sup.1--，--CH.sub.2--CHR.sup.1--CH.sub.2--，--CH.dbd.，--CH.dbd.CR.sup.1--或--CH.dbd.CR.sup.1--CH.dbd.，其中R.sup.1为--H，--Cl，--Br或--CH.sub.3，D为##STR3## 取决于端基B，X为--H，--Cl或--Br，Y为--H，C.sub.1-C.sub.7-烷基，--Cl，--Br，--CN，--CONH.sub.2--CO.sub.2R.sup.2，其中R.sup.2为H，C.sub.1-C.sub.6-烷基，C.sub.5-或C.sub.6-环烷基，C.sub.1-C.sub.4-烷氧基-C.sub.1-C.sub.4-烷基，C.sub.1-C.sub.4-烷基硫醇-C.sub.2-C.sub.4-烷基，丙炔基，苄基，α-苯乙基，α-苯丙基，C.sub.2-C.sub.4-烷基，其单取代，双取代或三取代由F或Cl取代，或CH.sub.3-取代或Cl-取代的烯丙基，Z为--COOR.sup.2，--CONR.sup.3R.sup.4，##STR4## 其中R.sup.3和R.sup.4均为H或C.sub.1-C.sub.4-烷基，或一起形成一个5-成员或6-成员的环状脂肪环，其碳链可以被氧原子中断。
• Amide compounds
  申请人：——

  公开号：US20040157866A1

  公开（公告）日：2004-08-12

  The present invention relates to compounds of the formula (I) wherein X 1 is wherein R 1 , R 2 and R 10 are independently hydrogen or a suitable substituent; R 11 and R 12 are independently hydrogen or a suitable substituent; R is unsaturated 5 to 6-membered heteromonocyclic group; A is direct bond or —NH—; X 2 is monocyclic arylene, unsaturated 5 to 6-membered heteromonocyclic group or cycloalkenylene; Y is bivalent group selected from ethylene, trimethylene and vinylene, wherein CH 2 is optionally replaced by NH or O, and CH is optionally replaced by N; and Z is —(CH 2 ) n —, —CO—(CH 2 ) m —, —CH═CH— or —CO—NH—, wherein n is 1, 2 or 3 and m is 1 or 2, or a salt thereof. The compounds of the present invention inhibit apolipoprotein B (Apo B) secretion and are useful as a medicament for prophylactic and treatment of diseases or conditions resulting from elevated circulating levels of Apo B. 1

  本发明涉及公式（I）的化合物，其中X1为R1，R2和R10分别为氢原子或适当的取代基；R11和R12分别为氢原子或适当的取代基；R为不饱和的5至6元杂环单环基；A为直接键或—NH—；X2为单环芳烃，不饱和的5至6元杂环单环基或环烯基；Y为乙烯基，三亚甲基或乙烯基中选择的双价基团，其中CH2可以被NH或O替代，CH可以被N替代；Z为—（ ）n—，—CO—（ ）m—，—CH=CH—或—CO—NH—，其中n为1、2或3，m为1或2，或其盐。本发明的化合物抑制载脂蛋白B（Apo B）的分泌，并可用作预防和治疗由于Apo B循环水平升高而导致的疾病或病症的药物。
• Synthesis and μ-opioid receptor affinity of a new series of nitro substituted 3,8-diazabicyclo[3.2.1]octane derivatives
  作者：D. Barlocco、G. Cignarella、P. Vianello、S. Villa、G.A. Pinna、P. Fadda、W. Fratta

  DOI：10.1016/s0014-827x(98)00065-2

  日期：1998.8

  A new series of analogues (1c-j; 2c-i) of the previously reported analgesic 3,8-diazabicyclo[3.2.1]octanes (1a,b; 2a,b) was synthesized and tested for their affinity towards mu-opioid receptors. Modifications were introduced either at the cinnamyl or the acyl side chains. The majority of the new compounds, with the exception of 1c,j and 2c, showed K-i values better or comparable with those of the models. (C) 1998 Elsevier Science S.A. All rights reserved.